Minocycline

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Names

[ CAS No. ]:
10118-90-8

[ Name ]:
Minocycline

[Synonym ]:
(4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboximidic acid
Minocyclin
Minocin
7-dimethylamino-6-demethyl-6-deoxytetracycline
(4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
4S-(4a,4aa,5aa,12aa)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacene carboxamide
Minocyclinum
[4S-(4a,4aa,5aa,12aa)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
Apo-Minocycline
(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
(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Minocycline
Arestin
7-(N,N-dimethylamino)sancycline
Aknemin
Minocyclinum [INN-Latin]
EINECS 237-099-7
Dynacin
Minociclina
MFCD00083669

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
803.3±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C23H27N3O7

[ Molecular Weight ]:
457.476

[ Flash Point ]:
439.6±34.3 °C

[ Exact Mass ]:
457.184906

[ PSA ]:
164.63000

[ LogP ]:
-0.65

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.718

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI7630000
CHEMICAL NAME :
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro -3,10,12,12a- tetrahydroxy-1,11-dioxo-
CAS REGISTRY NUMBER :
10118-90-8
LAST UPDATED :
199712
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C23-H27-N3-O7
MOLECULAR WEIGHT :
457.53
WISWESSER LINE NOTATION :
L E6 C666 BV FV CU GUTTT&J DQ EQ GMVH HQ IN1&1 ON1&1 RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
28 mg/kg/2W-I
TOXIC EFFECTS :
Brain and Coverings - changes in circulation (hemorrhage, thrombosis, etc.) Sense Organs and Special Senses (Eye) - visual field changes Behavioral - headache
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
343 mg/kg/17W-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), diffuse Liver - liver function tests impaired Blood - eosinophilia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
112 mg/kg/4W-I
TOXIC EFFECTS :
Liver - liver function tests impaired Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - interstitial nephritis Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - hematuria
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1204 mg/kg/86W-I
TOXIC EFFECTS :
Musculoskeletal - joints
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
730 mg/kg/1Y-I
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - nausea or vomiting Liver - liver function tests impaired
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
310 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
140 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - excitement Musculoskeletal - changes in teeth and supporting structures

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
3750 ug/L
REFERENCE :
BCPHBM British Journal of Clinical Pharmacology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1974- Volume(issue)/page/year: 16,127,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3732 No. of Facilities: 13 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 7704 (estimated) No. of Female Employees: 7190 (estimated)

Synthetic Route

Precursor & DownStream

Precursor

  • Minocycline hydrochloride
  • (dimethylamino)trimethyltin
  • 7-iodosancycline

DownStream

  • 9-Animominocycline

Related Compounds

  • 2-Cyclobutylimidazo[1,2-a]pyridine-3-sulfonyl fluoride
  • 2-(Butan-2-yl)-5-methylimidazo[1,2-a]pyridine-3-sulfonyl fluoride
  • 5-Methyl-2-(1-methylcyclopropyl)imidazo[1,2-a]pyridine-3-sulfonyl fluoride
  • 6-Methyl-2-(propan-2-yl)imidazo[1,2-a]pyridine-3-sulfonyl fluoride
  • 3,6-Diethylimidazo[2,1-b][1,3]thiazole-5-sulfonyl fluoride
  • 5-(3-Ethoxy-2-fluorophenyl)-2-methylaniline
  • 1-(4-Fluorobutyl)cyclopropane-1-sulfonyl chloride
  • 1-[(3-Chloro-2-fluorophenyl)methyl]cyclopropane-1-sulfonyl chloride
  • 1-(1-Cyanopropyl)cyclopropane-1-sulfonyl chloride
  • 1-[2-(4-Methyl-1,3-thiazol-5-yl)ethyl]cyclopropane-1-sulfonyl chloride
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