Demeclocycline

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Names

[ CAS No. ]:
127-33-3

[ Name ]:
Demeclocycline

[Synonym ]:
Ledermycin hydrochloride
7-chloro-6-demethyltetracycline
6-demethyl-7-chlorotetracycline
(2E,4S,4aS,5aS,6S,12aS)-2-[Amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
Elkamicina
DMCTC
(4aS)-7-Chlor-4c-dimethylamino-3,6t,10,12,12a-pentahydroxy-1,11-dioxo-(4ar,5ac,12ac)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacen-2-carbonsaeure-amid
Declomycin
EINECS 204-834-8
Demeclocyclinum
7-chloro-4-dimethylamino-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide
(2E,4S,4aS,5aS,6S,12aS)-2-[Amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5a,6,12a-tetrahydro-1,3,12(2H,4H,5H)-tetracenetrione
1,3,12(2H,4H,5H)-Naphthacenetrione, 2-(aminohydroxymethylene)-7-chloro-4-(dimethylamino)-4a,5a,6,12a-tetrahydro-6,10,11,12a-tetrahydroxy-, (2E,4S,4aS,5aS,6S,12aS)-
Demethylchlortetracycline(DMCT)
Demeclociclina
Ledermycin
domeclocycline
(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
684.5±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C21H21ClN2O8

[ Molecular Weight ]:
464.853

[ Flash Point ]:
367.8±31.5 °C

[ Exact Mass ]:
464.098633

[ PSA ]:
181.62000

[ LogP ]:
0.57

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.761

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI7650000
CHEMICAL NAME :
2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octah ydro- 3,6,10,12,12a-pentahydroxy-1,11-dioxo-
CAS REGISTRY NUMBER :
127-33-3
LAST UPDATED :
199706
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C21-H21-Cl-N2-O8
MOLECULAR WEIGHT :
464.89
WISWESSER LINE NOTATION :
L E6 C666 BV FV CU GUTTT&J DQ EQ GVZ HQ IN1&1 MQ OG RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
420 mg/kg/6W
TOXIC EFFECTS :
Endocrine - diabetes insipidus (nephrogenic or CNS) Biochemical - Metabolism (Intermediary) - effect on cyclic nucleotides
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
10 mg/kg
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
68 mg/kg/8D
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - other changes in urine composition
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>6750 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 - rat
DOSE/DURATION :
358 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 :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/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 :
454 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 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 :
79 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
240 mg/kg
SEX/DURATION :
female 1-39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other postnatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 gm/kg
SEX/DURATION :
female 1-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 gm/kg
SEX/DURATION :
female 1-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other postnatal measures or effects

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 - X5539 No. of Facilities: 10 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 330 (estimated) No. of Female Employees: 120 (estimated)

Precursor & DownStream

Precursor

DownStream

  • 4-Epidemeclocycline

Related Compounds

  • demeclocycline
  • 4-Epidemeclocycline
  • Demeclocycline calcium
  • Demeclocycline hydrochloride
  • Des(dimethylamino)-4-hydrazone Demeclocycline
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  • 5-(6-Methoxypyridin-2-yl)-1,3-oxazolidin-2-one
  • 4-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-(methylsulfanyl)butanamido]-3-methyloxolane-3-carboxylic acid
  • (2R,4R)-1-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-1,3-thiazole-4-carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
  • 3-{2-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]-3-methylbutanamido}benzoic acid
  • 2-(2-{[1-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)cyclopropyl]formamido}ethyl)benzoic acid
  • 4-{[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)furan-2-yl]formamido}-4-methylpentanoic acid
  • 2-{[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-fluorophenyl]formamido}pent-4-ynoic acid
  • 2-{1-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-fluorophenyl]-N-methylformamido}butanoic acid
  • 2-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2,3-trimethylbutanamido]-2-methylpentanoic acid