Minocycline
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| Category | Antibiotics |
| Catalog number | BBF-03789 |
| CAS | 10118-90-8 |
| Molecular Weight | 457.48 |
| Molecular Formula | C23H27N3O7 |
| Purity | 95% |
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Description
Minocycline is a broad-spectrum tetracycline antibiotic, which has a broader spectrum than the other members of the group. It is effective against tetracycline-resistant staphylococcus infections. It is a bacteriostatic antibiotic and is classified as a long-acting type. It is the most lipid-soluble of the tetracycline-class antibiotics, giving it the greatest penetration into the prostate and brain. It is not a naturally-occurring antibiotic, but was synthesized semi-synthetically from natural tetracycline antibiotics by Lederle Laboratories in 1966. It is mainly used for the treatment of acne and other skin infections. Its application is very limited because of its side effects.
Specification
| Related CAS | 13614-98-7 (hydrochloride) |
| Synonyms | Minostad; Akamin; Minocin; Minoderm; Cyclimycin; Solodyn; Dynacin; Sebomin; Divaine; Tigecycline EP Impurity C |
| Shelf Life | 2 month in rt, long time |
| Storage | Store at -20°C (dark) |
| IUPAC Name | (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide |
| Canonical SMILES | CN(C)C1C2CC3CC4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C |
| InChI | InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1 |
| InChI Key | FFTVPQUHLQBXQZ-KVUCHLLUSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Orange Solid |
| Antibiotic Activity Spectrum | bacteria |
| Boiling Point | 659.401°C at 760 mmHg |
| Density | 1.553 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Preventive effects of minocycline in a neurodevelopmental two-hit model with relevance to schizophrenia.
Giovanoli S1,2, Engler H3, Engler A3, Richetto J4,5,6, Feldon J2, Riva MA4,5, Schedlowski M3, Meyer U1,2,6. Transl Psychiatry. 2016 Apr 5;6:e772. doi: 10.1038/tp.2016.38.
Maternal immune activation can increase the vulnerability of the offspring to develop neuroimmune and behavioral abnormalities in response to stress in puberty. In offspring of immune-challenged mothers, stress-induced inflammatory processes precede the adult onset of multiple behavioral dysfunctions. Here, we explored whether an early anti-inflammatory intervention during peripubertal stress exposure might prevent the subsequent emergence of adult behavioral pathology. We used an environmental two-hit model in mice, in which prenatal maternal administration of the viral mimetic poly(I:C) served as the first hit, and exposure to sub-chronic unpredictable stress during peripubertal maturation as the second hit. Using this model, we examined the effectiveness of the tetracycline antibiotic minocycline (MINO) given during stress exposure to block stress-induced inflammatory responses and to prevent subsequent behavioral abnormalities. We found that combined exposure to prenatal immune activation and peripubertal stress caused significant deficits in prepulse inhibition and increased sensitivity to the psychotomimetic drugs amphetamine and dizocilpine in adulthood.
2.Rabeprazole, Minocycline, Amoxicillin, and Bismuth as First-Line and Second-Line Regimens for Helicobacter pylori Eradication.
Song Z1, Suo B1, Zhang L1, Zhou L1. Helicobacter. 2016 Apr 6. doi: 10.1111/hel.12313. [Epub ahead of print]
BACKGROUND: Because of general unavailability of tetracycline, common adverse effects, and complicated administration, the clinical application of bismuth quadruple therapy often faces difficulties. Whether the combination of minocycline and amoxicillin can replace tetracycline and metronidazole for Helicobacter pylori eradication remains unclear. This study was to determine the efficacy, compliance, and safety of rabeprazole, minocycline, amoxicillin, and bismuth (RMAB) therapy as first-line and second-line regimens.
3.Empirical therapy in Methicillin-resistant Staphylococcus Aureus infections: An Up-To-Date approach.
VanEperen AS1, Segreti J2. J Infect Chemother. 2016 Apr 8. pii: S1341-321X(16)30009-5. doi: 10.1016/j.jiac.2016.02.012. [Epub ahead of print]
Methicillin-resistant Staphylococcus aureus (MRSA) continues to be an important pathogen worldwide, with high prevalence of infection in both community and hospital settings. Timely and appropriate choice of empirical therapy in the setting of MRSA infection is imperative due to the high rate of associated morbidity and mortality with MRSA infections. Initial choices should be made based on the site and severity of the infection, most notably moderate skin and soft tissue infections which may be treated with oral antibiotics (trimethoprim-sulfamethoxazole, clindamycin, doxycycline/minocycline, linezolid) in the outpatient setting, versus choice of parenteral therapy in the inpatient setting of more invasive or severe disease. Though the current recommendations continue to strongly rely on vancomycin as a standard empiric choice in the setting of severe/invasive infections, alternative therapies exist with studies supporting their non-inferiority.
4.Severe and Persistent Thyroid Dysfunction Associated with Tetracycline-Antibiotic Treatment in Youth.
Pollock AJ1, Seibert T2, Allen DB3. J Pediatr. 2016 Apr 5. pii: S0022-3476(16)00415-7. doi: 10.1016/j.jpeds.2016.03.034. [Epub ahead of print]
Thyroid dysfunction in adolescents treated with minocycline for acne has been previously described as transient effect and/or associated with autoimmune thyroiditis. We report nonimmune-mediated thyroid dysfunction associated with minocycline/doxycycline in 3 adolescents whose clinical courses suggest an adverse effect that may be more common, serious, and persistent than realized previously.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
