Anthramycin

Modify Date: 2024-01-06 18:14:29

Anthramycin Structure
Anthramycin structure
Common Name Anthramycin
CAS Number 4803-27-4 Molecular Weight 315.32400
Density 1.505 g/cm3 Boiling Point 679.872ºC at 760mmHg
Molecular Formula C16H17N3O4 Melting Point 188-194ºC
MSDS N/A Flash Point 364.974ºC

 Use of Anthramycin


Anthramycin, a member of the pyrolobenzodiazepine (PBD) family, is a potent antibiotic. Anthramycin has potent antitumor activity. Anthramycin can act as an potent antagonist of cholecystokinin in the central nervous system in mice[1][2][3].

 Names

Name Anthramycin
Synonym More Synonyms

 Anthramycin Biological Activity

Description Anthramycin, a member of the pyrolobenzodiazepine (PBD) family, is a potent antibiotic. Anthramycin has potent antitumor activity. Anthramycin can act as an potent antagonist of cholecystokinin in the central nervous system in mice[1][2][3].
Related Catalog
In Vitro ANT is delivered through the skin for PG (propylene glycol), TC (Transcutol P) and PGML (propylene glycol monolaurate) with the active “tracking” the skin penetration of both PG and TC[1]. Anthramycin (10-1000 μM) dose not affect the ATPase activity of heart mitochondria[3].
In Vivo Anthramycin (0-0.5 mg/kg, IP, once) has potent anti-CCK (cholecystokinin) activity and antinociceptive effects in the central nervous system in mice[2]. Anthramycin (0.1-0.5 mg/kg, SC, daily for 8 days) has no effect on mitochondrial metabolism of the rat heart[3]. Animal Model: Male ddY mice (20 ± 2 g, 12-14 each group)[2] Dosage: 0, 0.3, and 0.5 mg/kg Administration: IP, once, 10 min before the intracisternal (i.c.) injection of CCK Result: Significantly inhibited CCK-induced increase in the pain threshold in a dose-dependent manner. Almost completely suppressed the antinociceptive effects of CCK at the higher dose (0.5 mg/kg). Animal Model: Female CFN Gif rats (140-180 g)[3] Dosage: 0.1 mg/kg, 0.25 mg/kg, and 0.5 mg/kg Administration: SC, daily for 8 days Result: Recorded no differences between anthramycin- and DMSO-treated rats with respect to P/O ratios, respiration rates, and ATPase activity of heart mitochondria.
References

[1]. Haque T, et al. Topical delivery of anthramycin II. Influence of binary and ternary solvent systems. Eur J Pharm Sci. 2018 Aug 30;121:59-64.

[2]. Kubota K, et al. Cholecystokinin antagonism by anthramycin, a benzodiazepine antibiotic, in the central nervous system in mice. Brain Res. 1989 Apr 17;485(1):62-6.

[3]. Cargill C, et al. Effects of daunomycin and anthramycin on electrocardiogram and mitochondrial metabolism of the rat heart. J Natl Cancer Inst. 1974 Aug;53(2):481-6.

 Chemical & Physical Properties

Density 1.505 g/cm3
Boiling Point 679.872ºC at 760mmHg
Melting Point 188-194ºC
Molecular Formula C16H17N3O4
Molecular Weight 315.32400
Flash Point 364.974ºC
Exact Mass 315.12200
PSA 115.89000
LogP 1.36060
Index of Refraction 1.723

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY8429000
CHEMICAL NAME :
1H-Pyrrolo(2,1-c)(1,4)benzodiazepine-2-acrylamide, 5,10,11,11a-tetrahydro-9,11-dihydroxy-8- methyl-5-oxo-, (E)-
CAS REGISTRY NUMBER :
4803-27-4
LAST UPDATED :
199712
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C16-H17-N3-O4
MOLECULAR WEIGHT :
315.36
WISWESSER LINE NOTATION :
T C576 BVN IM DUTT&J E1U1VZ HQ KQ L1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
650 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Unscheduled DNA synthesis
TEST SYSTEM :
Human Fibroblast
DOSE/DURATION :
200 nmol/L
REFERENCE :
JBCHA3 Journal of Biological Chemistry. (428 E. Preston St., Baltimore, MD 21202) V.1- 1905- Volume(issue)/page/year: 254,605,1979

 Synonyms

(11R,11aS)-5,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo<2,1-c><1,4>benzodiazepin-2-trans-acrylamid
3-(9,11-dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-2-yl)-acrylamide
Antramycin