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Minocycline
Systematic (IUPAC) name
(2E,4S,4aR,5aS,12aR)- 2-(amino-hydroxy-methylidene)- 4,7-bis(dimethylamino)- 10,11,12a-trihydroxy-4a,5,5a,6- tetrahydro-4H-tetracene- 1,3,12-trione[1]
Identifiers
CAS number 10118-90-8
ATC code J01AA08 A01AB23
PubChem 24960
DrugBank APRD00547
Chemical data
Formula C23H27N3O7 
Mol. mass 457. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. ATC code A01 is a division of the Anatomical Therapeutic Chemical Classification System and part of the A Alimentary tract and metabolism section PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 477
Pharmacokinetic data
Bioavailability 100%
Metabolism liver
Half life 11-22 hours
Excretion mostly fecal, rest renal
Therapeutic considerations
Pregnancy cat.

?
Legal status

Prescription Only (S4)(AU)
Routes oral

Minocycline hydrochloride, also known as minocycline, is a member of the broad spectrum tetracycline antibiotics, and has a broader spectrum than the other members. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The liver is a vital organ in the human body and is present in Vertebrates and some other animals The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials Feces, faeces, or fæces (see spelling differences) is a waste product from an animal's digestive tract expelled through the Anus The kidneys are complicated organs that have numerous biological roles The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. For a topic outline on this subject see List of basic Australia topics. In Pharmacology and Toxicology, a route Tetracyclines are a group of Broad-spectrum antibiotics whose general usefulness has been reduced with the onset of bacterial resistance It is a bacteriostatic antibiotic. Bacteriostatic Antibiotics limit the growth of bacteria by interfering with bacterial Protein production DNA replication or other aspects of As a result of its long half-life it generally has serum levels 2-4 times that of most other tetracyclines (150 mg giving 16 times the activity levels compared to 250 mg of tetracycline at 24-48 hours). Blood plasma is the Liquid component of Blood, in which the Blood cells are suspended This article deals with the specific antibiotic called tetracycline Minocycline was originally discovered by Lederle Laboratories and marketed under the brand name Minocin. American Cyanamid is a large diversified American chemical manufacturer founded by Frank Washburn in 1907 [2]

Contents

Indications

Minocycline 100 mg Capsules.
Minocycline 100 mg Capsules.

It is primarily used to treat acne and other skin infections as well as lyme disease as the one pill twice daily 100 mg dosage is far easier for patients than the four times a day required with tetracycline or oxytetracycline. Acne vulgaris (commonly called acne) is a Skin disease caused by changes in the Pilosebaceous units (skin structures consisting of a Hair follicle Oxytetracycline was the second of the broad-spectrum tetracycline group of Antibiotics to be discovered

Although minocycline's broader spectrum of activity, compared to other members of the group, includes activity against Neisseria meningitidis, its use as a prophylaxis is no longer recommended because of side effects (dizziness and vertigo). Neisseria meningitidis, also simply known as meningococcus, is a heterotrophic Gram-negative diplococcal Bacterium best known for Prophylaxis ( Greek "προφυλάσσω" to guard or prevent beforehand) is any medical or Public health procedure whose purpose Vertigo (from the Latin vertere, to turn and the suffix -igo, a condition i

It may be used to treat certain strains of MRSA infection and disease caused by drug resistant Acinetobacter. Acinetobacter is a Gram-negative Genus of bacteria belonging to the Phylum Proteobacteria.

For other uses of minocycline see Tetracycline antibiotics and oxytetracycline as the uses are much the same between Tetracyclines with only minor exceptions. Tetracyclines are a group of Broad-spectrum antibiotics whose general usefulness has been reduced with the onset of bacterial resistance Oxytetracycline was the second of the broad-spectrum tetracycline group of Antibiotics to be discovered

Cautions

Contrary to all the other tetracycline antibiotics (Doxycycline excluded), minocycline may be used in renal impairment, but may aggravate systemic lupus erythematosus. Doxycycline ( INN) (ˌdɒksɪˈsaɪkliːn is a member of the Tetracycline antibiotics group and is commonly used to treat a variety of Infections Doxycycline Systemic lupus erythematosus ( SLE or lupus,) is a chronic autoimmune disease that can be fatal though with recent medical advances fatalities are becoming [3]

Also, more so than other tetracyclines, minocycline can cause the rare condition of secondary intracranial hypertension which has initial symptoms of headache, visual disturbances, and confusion. Cerebral edema, as well as autoimmune Rheumatoid Arthritis are rare side effects to Minocycline in some people. Cerebral edema (cerebral oedema in British English) is an excess accumulation of water in the intracellular and/or extracellular spaces of the Brain. Rheumatoid arthritis ( RA) is a chronic systemic autoimmune disorder that causes the Immune system to attack the Joints, where [4]

Minocycline, like all tetracyclines, becomes dangerous past its expiration date. While most prescription drugs lose potency after their expiration dates, tetracyclines were known to become toxic over time due to the breakdown of certain chemicals present in the manufactured capsules. This is not a present concern in drugs manufactured in first world countries. Expired tetracyclines, as previously manufactured, can cause serious damage to the kidneys.

Minocycline's absorption is impaired if taken at the same time of day as calcium or iron supplements. Unlike some of the other tetracycline group antibiotics, it can be taken with calcium-rich foods such as milk, although this does reduce the absorption slightly. [5] In a recent news item in Science dated 23 November 2007, it has been mentioned that MINOCYCLINE in ALS is harmful. Amyotrophic Lateral Sclerosis ( ALS, sometimes called Maladie de Charcot, or in the United States Lou Gehrig's Disease) is a progressive Patients on minocycline declined more rapidly than those on placebo. At present the mechanism of this side effect is unknown. According to the researcher from Columbia University the effect does not seem to be dose dependent because the patients on high doses did not do worse than those on the low doses. Science Vol 318, 1227, 2007.

Side effects

This medication may cause upset stomach, diarrhea, dizziness, unsteadiness, drowsiness, headache or vomiting. In Medicine, diarrhea, also spelled diarrhoea (see spelling differences) is frequent loose or liquid Bowel movements Acute diarrhea Many different terms are often used to describe what is collectively known as dizziness. Somnolence (or " drowsiness " is a state of near- Sleep, a strong desire for sleep or sleeping for unusually long periods (c A headache ( cephalalgia in medical terminology is a condition of pain in the Head; sometimes Neck or upper back pain may also be interpreted Vomiting (also called throwing up, emesis) is the forceful expulsion of the contents of one's Stomach through the Mouth and sometimes the If these symptoms persist or worsen, one should notify their doctor. Minocycline increases sensitivity to sunlight. Photophobia is a Symptom of excessive sensitivity to Light and the aversion to Sunlight or well-lit places It has also been linked to cases of lupus, although rarely. Prolonged sun exposure should be avoided. Wear protective clothing and use a sunscreen if needed. Sunscreen (also known as sunblock or suntan lotion) is a Lotion, spray or other Topical product that absorbs or reflects the Sun 's Very unlikely but should be reported: fever, yellowing of the eyes or skin, stomach pain, sore throat, vision changes and mental changes. Fever (also known as pyrexia, from the Greek pyretos meaning fire or a febrile response, from the Latin word Febris Jaundice, also known as icterus (attributive adjective "icteric" is yellowish discoloration of the Skin, sclerae (whites of the eyes

In those cases where this drug must be used for extended periods, blue-gray skin discoloration may occur. In the unlikely event one has an allergic reaction to this drug, immediate medical attention should be sought. Allergy is a disorder of the Immune system often also referred to as Atopy. Symptoms of an allergic reaction include rash, itching, swelling, severe dizziness, trouble breathing. A rash is a change of the Skin which affects its color appearance or Texture. Many different terms are often used to describe what is collectively known as dizziness. This drug has also been reported to cause Idiopathic intracranial hypertension (Pseudotumor Cerebri). Idiopathic intracranial hypertension (IIH sometimes called benign intracranial hypertension (BIH or pseudotumor cerebri (PTC is a Neurological disorder This happened in case of a young 18 year old girl in New Delhi. She was prescribed minocycline for her acne and after taking the drug for almost a month, she started having constant headaches and blurred vision. She consulted a neurologist for her headaches who found that she had raised intra cranial pressure and traced that to her prescription minocycline. Other effects not listed above should be reported to the doctor or pharmacist.

Uses

Anti-inflammatory and neuroprotective

Current research is examining the possible neuroprotective and anti-inflammatory effects of minocycline against progression of a group of neurodegenerative disorders including multiple sclerosis (MS), rheumatoid arthritis (RA), amyotrophic lateral sclerosis (ALS), Huntington's disease, and Parkinsons disease,[6] amongst others neurodegenerative diseases. Acne vulgaris (commonly called acne) is a Skin disease caused by changes in the Pilosebaceous units (skin structures consisting of a Hair follicle Dysentery (formerly known as flux or the bloody flux) is an infection of the digestive system that results in severe Diarrhea containing mucus and blood Anthrax is an acute Disease in humans and animals caused by the bacterium Bacillus anthracis which is highly lethal in some forms Cholera, sometimes known as Asiatic cholera or epidemic cholera, is an infectious Gastroenteritis caused by the Bacterium Gonorrhea (also gonorrhoea) caused by the bacteria Neisseria gonorrhoeae, is a common Sexually transmitted disease. Penicillin (sometimes abbreviated PCN or pen) is a group of Beta-lactam antibiotics used in the treatment of Bacterial Infections Lyme disease, or borreliosis, is an Emerging infectious disease caused by at least three Species of Bacteria belonging to the Genus Bubonic plague is the best-known manifestation of the bacterial disease plague, caused by the bacterium Yersinia pestis (formerly known as Pneumonia is an inflammatory illness of the Lung. Frequently it is described as lung Parenchyma / alveolar inflammation and abnormal Rocky Mountain spotted fever is the most severe and most frequently reported Rickettsial illness in the United States. Syphilis is a Sexually transmitted disease caused by the spirochetal Bacterium Treponema pallidum pallidum. A urinary tract infection ( UTI) is a bacterial Infection that affects any part of the Urinary tract. The cervix (from Latin "neck" is the lower narrow portion of the Uterus where it joins with the top end of the Vagina. Neurodegenerative Disease ( Greek νέυρο- néuro-, "nerval" and Latin dēgenerāre, "to decline" or "to Multiple sclerosis (abbreviated MS also known as disseminated sclerosis or encephalomyelitis disseminata) is an autoimmune condition in which the Rheumatoid arthritis ( RA) is a chronic systemic autoimmune disorder that causes the Immune system to attack the Joints, where Amyotrophic Lateral Sclerosis ( ALS, sometimes called Maladie de Charcot, or in the United States Lou Gehrig's Disease) is a progressive Huntington's disease, also called Huntington's chorea, chorea major, or HD, is a genetic neurological disorder characterized after Parkinson's disease (also known as Parkinson disease or PD) is a degenerative disorder of the Central nervous system that often impairs the sufferer's [7][8][9]

The neuroprotective action of minocycline may include its inhibitory effect on 5-lipoxygenase, [10] an inflammatory enzyme associated with brain aging, and is being studied for use in Alzheimer's disease patients. The GNF_Protein_box is automatically maintained by Protein Box Bot Alzheimer's disease ( AD) also called Alzheimer disease or simply Alzheimer's, is the most common form of Dementia. [11] It also has been used as a "last ditch" treatment for toxoplasmosis in AIDS patients. Toxoplasmosis is a Parasitic disease caused by the Protozoan Toxoplasma gondii. Minocycline is neuroprotective in mouse models of amyotrophic lateral sclerosis (ALS) and Huntington's disease and has been recently shown to stabilize the course of Huntington's disease in humans over a 2-year period.

As an anti-inflammatory, minocycline inhibits apoptosis (cell death) via attenuation of TNF-alpha, downregulating pro-inflammatory cytokine output. Tumor necrosis factor ( TNF, cachexin or cachectin and formally known as Tumor necrosis factor-alpha) is a Cytokine involved in systemic Cytokines are a category of signalling Proteins and Glycoproteins that like Hormones and Neurotransmitters, are used extensively in cellular This effect is mediated by a direct action of minocycline on the activated T cells and on microglia, which results in the decreased ability of T cells to contact microglia which impairs cytokine production in T cell-microglia signal transduction . T cells belong to a group of White blood cells known as Lymphocytes, and play a central role in Cell-mediated immunity. Microglia are a type of Glial cell that acts as the first and main form of active immune defense in the Central nervous system (CNS In Biology, signal transduction refers to any process by which a cell converts one kind of signal or stimulus into another [12] Minocycline also inhibits microglial activation, through blockade of NF-kappa B nuclear translocation. NF-κB ( nuclear factor-kappa B) is a protein complex that is a Transcription factor.

It is thought that minocycline exerts neuroprotective effects independent of its anti-inflammatory properties. [13]

A recent study reported the impact of the antibiotic minocycline on clinical and magnetic resonance imaging (MRI) outcomes and serum immune molecules in MS patients over 24 months of open-label minocycline treatment. Despite a moderately high pretreatment relapse rate in patients in the study prior to treatment, no relapses occurred between months 6 and 24. The only patient with gadolinium-enhancing lesions on MRI at 12 and 24 months was on half-dose minocycline. Gadolinium (ˌgædəˈlɪniəm is a Chemical element that has the symbol Gd and Atomic number 64 Levels of interleukin-12 (IL-12), which at high levels might antagonize the proinflammatory IL-12 receptor, were elevated over 18 months of treatment, as were levels of soluble vascular cell adhesion molecule-1 (VCAM-1). For Il-12 see also Ilyushin Il-12 Interleukin 12 ( IL-12) is an Interleukin that is naturally produced by Dendritic The blood vessels are part of the Circulatory system and function to transport Blood throughout the body Cell Adhesion Molecules ( CAM s are Proteins located on the cell surface involved with the Binding with other cells or with the Extracellular Vascular cell adhesion molecule 1, also known as VCAM1, is a human Gene. The activity of matrix metalloproteinase-9 was decreased by treatment. Matrix metalloproteinases (MMPs are Zinc -dependent Endopeptidases other family members are Adamalysins Serralysins and Astacins Clinical and MRI outcomes in this study were supported by systemic immunological changes and call for further investigation of minocycline in MS. [14][15][13][16]

A recent study (2007) found that patients taking 200 mg of minocycline for 5 days within 24 hours of an ischemic stroke showed an improvement in functional state and stroke severity over a period of 3 months compared with patients receiving placebo. [17]

Trade names and availability

Minocycline is no longer covered by patent and is therefore marketed under several trade names:

StoneBridge Pharma also markets Minocycline as Cleeravue-M in combination with SteriLid eyelid cleanser in the treatment of rosacea blepharitis. Rosacea (rəʊˈzeɪʃə is a common but often misunderstood condition that is estimated to affect over 45 million people worldwide Blepharitis /ˌblɛfɚˈɑɪ̯tɪs/ is an Ocular Disease characterized by Inflammation of the Eyelid margins

References

  1. ^ DrugBank: DB01017 (Minocycline)
  2. ^ [1]Lin, DW The Tetracyclines March 2005
  3. ^ Gough A, Chapman S, Wagstaff K, Emery P, Elias E (1996). "Minocycline induced autoimmune hepatitis and systemic lupus erythematosus-like syndrome". BMJ 312 (7024): 169-72. PMID 8563540.  
  4. ^ Lefebvre N, Forestier E, Farhi D, et al. (2007). "Minocycline-induced hypersensitivity syndrome presenting with meningitis and brain edema: a case report". Journal of Medical Case Reports 1: 22. doi:10.1186/1752-1947-1-22. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  5. ^ Piscitelli, Stephen C. ; Keith Rodvold (2005). Drug Interactions in Infectious Diseases. Humana Press. ISBN 1588294552.  
  6. ^ National Institute of Health (February 23, 2006). "Preliminary Study Shows Creatine and Minocycline May Warrant Further Study In Parkinson’s Disease". Press release. A news release, media release, press release or press statement is a written or recorded Communication directed at members of the News
  7. ^ Chen M, Ona VO, Li M, Ferrante RJ, Fink KB, Zhu S, Bian J, Guo L, Farrell LA, Hersch SM, Hobbs W, Vonsattel JP, Cha JH, Friedlander RM (2000). "Minocycline inhibits caspase-1 and caspase-3 expression and delays mortality in a transgenic mouse model of Huntington disease". Nat Med 6 (7): 797-801. doi:10.1038/80538. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 10888929.  
  8. ^ Tikka TM, Koistinaho JE (2001). "Minocycline provides neuroprotection against N-methyl-D-aspartate neurotoxicity by inhibiting microglia". J Immunol 166 (12): 7527-33. PMID 11390507.  
  9. ^ Nirmalananthan N, Greensmith L (2005). "Amyotrophic lateral sclerosis: recent advances and future therapies". Curr. Opin. Neurol. 18 (6): 712-9. doi:10.1097/01.wco.0000187248.21103.c5. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 16280684.  
  10. ^ Song Y, Wei EQ, Zhang WP, Zhang L, Liu JR, Chen Z (2004). "Minocycline protects PC12 cells from ischemic-like injury and inhibits 5-lipoxygenase activation". Neuroreport 15 (14): 2181-4. doi:10.1097/00001756-200410050-00007. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15371729.  
  11. ^ Uz T, Pesold C, Longone P, Manev H (1998). "Aging-associated up-regulation of neuronal 5-lipoxygenase expression: putative role in neuronal vulnerability". FASEB J 12 (6): 439-49. PMID 9535216.  
  12. ^ Giuliani F, Hader W, Yong VW (2005). "Minocycline attenuates T cell and microglia activity to impair cytokine production in T cell-microglia interaction". J. Leukoc. Biol. 78 (1): 135-43. doi:10.1189/jlb.0804477. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15817702.  
  13. ^ a b Maier K, Merkler D, Gerber J, Taheri N, Kuhnert AV, Williams SK, Neusch C, Bähr M, Diem R (2007). "Multiple neuroprotective mechanisms of minocycline in autoimmune CNS inflammation". Neurobiol. Dis. 25 (3): 514-25. doi:10.1016/j.nbd.2006.10.022. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 17239606.  
  14. ^ Zabad RK, Metz LM, Todoruk TR, Zhang Y, Mitchell JR, Yeung M, Patry DG, Bell RB, Yong VW (2007). "The clinical response to minocycline in multiple sclerosis is accompanied by beneficial immune changes: a pilot study". Mult. Scler. 13 (4): 517-26. doi:10.1177/1352458506070319. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 17463074.  
  15. ^ Zemke D, Majid A (2004). "The potential of minocycline for neuroprotection in human neurologic disease". Clinical neuropharmacology 27 (6): 293-8. doi:10.1097/01.wnf.0000150867.98887.3e. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15613934.  
  16. ^ Popovic N, Schubart A, Goetz BD, Zhang SC, Linington C, Duncan ID (2002). "Inhibition of autoimmune encephalomyelitis by a tetracycline". Ann. Neurol. 51 (2): 215-23. doi:10.1002/ana.10092. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 11835378.  
  17. ^ Lampl Y, Boaz M, Gilad R, et al (2007). "Minocycline treatment in acute stroke: an open-label, evaluator-blinded study". Neurology 69 (14): 1404–10. doi:10.1212/01.wnl.0000277487.04281.db. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 17909152.  

External links

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Dictionary

minocycline

-noun

  1. A tetracycline antibiotic used to treat bacterial and other infections
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