93908-02-2

93908-02-2 structure

Name: Rebeccamycin
Chemical Name: rebeccamycin
CAS Number: 93908-02-2
Molecular Formula: C₂₇H₂₁Cl₂N₃O₇
Molecular Weight: 570.37800
Catalog: Signaling Pathways Antibody-drug Conjugate ADC Cytotoxin
Create Date: 2018-07-09 14:22:21
Modify Date: 2024-01-05 16:22:48
Rebeccamycin, an antitumor antibiotic, inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I and has negligible effect on protein kinase C and topoisomerase II[1][2].

Name	rebeccamycin
Synonyms	AmbotzLS-1199 MFCD01718312

Description	Rebeccamycin, an antitumor antibiotic, inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I and has negligible effect on protein kinase C and topoisomerase II[1][2].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin
Target	Topoisomerase I Traditional Cytotoxic Agents
In Vitro	Rebeccamycin is an antitumor antibiotic produced by the actinomycete Saccharotrix aerocolonigenes with activity against several human tumor cell lines, including A549 (lung adenocarcinoma), HCT-116 (colon carcinoma), and KB (nasopharyngeal carcinoma) [1]. Rebeccamycin shows antibacterial activity against several Gram-positive bacteria, including Staphylococcus aureus and Streptococcus faecalis[3].
In Vivo	Rebeccamycin (2-256 mg/kg; i.p.; daily for 9 days) prolongs survival in B16 melanoma, L1210 leukemia[2]. Animal Model: CDF1 mice (B16 melanoma, L1210 leukemia)[2] Dosage: 2, 4, 8, 16, 32, 64, 128, 256 mg/kg Administration: I.p.; daily for 9 days Result: Prolongation of survival of the mice at dose levels ranging from 8 to 256 mg/kg.
References	[1]. Merchant J, et al. Phase I clinical and pharmacokinetic study of NSC 655649, a rebeccamycin analogue, given in both single-dose and multiple-dose formats. Clin Cancer Res. 2002 Jul;8(7):2193-201. [2]. Bush JA, et al. Production and biological activity of rebeccamycin, a novel antitumor agent. J Antibiot (Tokyo). 1987 May;40(5):668-78. [3]. Sánchez C, et al. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem Biol. 2002 Apr;9(4):519-31.

Density	1.87g/cm3
Molecular Formula	C₂₇H₂₁Cl₂N₃O₇
Molecular Weight	570.37800
Exact Mass	569.07600
PSA	150.37000
Index of Refraction	1.844

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM3455000

CHEMICAL NAME :: 5H-Indolo(2,3-a)pyrrolo(3,4-c)carbazole-5,7(6H)-dione , 1,11-dichloro-12,13-dihydro-12-(4-O- methyl-beta-D-glucopyranosyl)-

CAS REGISTRY NUMBER :: 93908-02-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C27-H21-Cl2-N3-O7

MOLECULAR WEIGHT :: 570.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Cells - not otherwise specified

DOSE/DURATION :: 3 mg/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 40,668,1987

RIDADR	NONH for all modes of transport

502498-34-2

93908-02-2

Literature: Kaneko; Wong; Okamoto; Clardy Tetrahedron Letters, 1985 , vol. 26, # 34 p. 4015 - 4018

102147-53-5

93908-02-2

Literature: Kaneko; Wong; Okamoto; Clardy Tetrahedron Letters, 1985 , vol. 26, # 34 p. 4015 - 4018

102147-55-7

93908-02-2

Literature: Kaneko; Wong; Okamoto; Clardy Tetrahedron Letters, 1985 , vol. 26, # 34 p. 4015 - 4018

Precursor 1
502498-34-2
DownStream 0

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