CAS 4803-27-4|Anthramycin

Introduction：Basic information about CAS 4803-27-4|Anthramycin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Anthramycin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Synonyms

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	/	Flash Point	364.974ºC

Names

Name	Anthramycin
Synonym	More Synonyms

Anthramycin BiologicalActivity

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	Research Areas >>CancerSignaling Pathways >>GPCR/G Protein >>Cholecystokinin Receptor
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
InChIKey	VGQOVCHZGQWAOI-YQRHFANHSA-N
SMILES	Cc1ccc2c(c1O)NC(O)C1CC(C=CC(N)=O)=CN1C2=O

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

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