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125317-39-7

125317-39-7 structure
125317-39-7 structure
  • Name: Vinorelbine (ditartrate)
  • Chemical Name: vinorelbine L-tartrate
  • CAS Number: 125317-39-7
  • Molecular Formula: C53H66N4O20
  • Molecular Weight: 1079.106
  • Catalog: API Antineoplastic agents Antimetabolite antineoplastic
  • Create Date: 2018-07-16 19:19:11
  • Modify Date: 2024-01-02 14:01:53
  • Vinorelbine (ditartrate) is an anti-mitotic agent which inhibits the proliferation of Hela cells with IC50 of 1.25 nM.
Name vinorelbine L-tartrate
Synonyms methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-15-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate bis(2,3-dihydroxybutanedioate) (salt)
aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,3β,4β,5α,12β,19α)-, 2,3-dihydroxybutanedioate (1:2) (salt)
MFCD03613607
methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate bis(2,3-dihydroxybutanedioate) (salt)
Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate 2,3-dihydroxysuccinate (1:2)
Vinorelbine Ditartarate
methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-15-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-1
Nor-5'-anhydrovinblastine ditartrate
Vinorelbine ditartrate salt
Eunades
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, m ;ethyl ester, (2β,3β,4β,5α,12β,19α)-, 2,3-dihydroxybutanedioate (1:2) (salt)
Vinorelbine tartrate
-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate bis(2,3-dihydroxybutanedioate) (salt)
methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-15-[(6R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate 2,3-dihydroxybutanedioate (1:2)
6-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate bis(2,3-dihydroxybutanedioate) (salt)
2,3-Dihydroxybutandisäure-methyl-(3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-5-carboxylat(2:1)
aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, m
ethyl ester, (2β,3β,4β,5α,12β,19α)-, 2,3-dihydroxybutanedioate (1:2) (salt)
Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate bis(2,3-dihydroxysuccinate) (salt)
Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-me
 thoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate 2,3-dihydroxysuccinate (1:2)
3',4'-Didehydro-4'-deoxy-C'-norvincaleukoblastine (R-(R*,R*))-2,3-dihydroxybutanedioate (1:2) (salt)
acide 2,3-dihydroxybutanedioïque - (3aR,4R,5S,5aR,10bR,13aR)-4-(acétyloxy)-3a-éthyl-9-[(12S,14R)-16-éthyl-12-(méthoxycarbonyl)-1,10-diazatétracyclo[12.3.1.0.0]octadéca-3(11),4,6,8,15-pentaén-12-yl]-5-hydroxy-8-méthoxy-6-méthyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate de méthyle (2:1)
methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-5-hydroxy-8-methoxy
Vinorelbine ditartrate
Methyl (3aR,4R,5S,5aR,10bR,13aR)-4-acetoxy-3a-ethyl-9-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate bis(2,3-dihydroxysuccinate) (salt)
Vinorelbine
Vinorelbine (ditartrate)
Description Vinorelbine (ditartrate) is an anti-mitotic agent which inhibits the proliferation of Hela cells with IC50 of 1.25 nM.
Related Catalog
In Vitro Vinorelbine (0.5-5 nM) inhibits cell proliferation by 50% (IC50) at concentrations of 1.25 nM. At concentration of 8 nM vinorelbine, no cells are in anaphase[1]. Vinorelbine time-dependently induces the p53 and p21WAFI/CIP1 expression in androgen-dependent (AD) and- independent (AI) prostate cancer cell lines. Vinorelbine stimulates reporter genes in a concentration-dependent manner[2].
In Vivo After vinorelbine treatment, the first neutropenicepisode occurred after the first (4 dogs), second (1), or sixth(1) vinorelbine treatment in the dogs[3]. Vinorelbine is tolerated at a weekly interval in tumor-bearing cats, with an MTD of 11.5 mg/m2[4].
Animal Admin As defined by the study, VRL1 is diluted in 0.9% NaCl to a concentration of 1.5 mg/mL, and given IV over 5 minutes. The intended treatment interval is 7 days for up to 4 treatments. After receiving 4 weekly doses, cats are eligible to continue VRL treatment every 2 weeks.
References

[1]. Ngan VK, et al. Mechanism of mitotic block and inhibition of cell proliferation by the semisynthetic Vinca alkaloids vinorelbine and its newer derivative vinflunine. Mol Pharmacol. 2001 Jul;60(1):225-32.

[2]. Liu XM, et al. Unique induction of p21(WAF1/CIP1)expression by vinorelbine in androgen-independent prostate cancer cells. Br J Cancer. 2003 Oct 20;89(8):1566-73.

[3]. Poirier VJ, et al. Toxicity, dosage, and efficacy of vinorelbine (Navelbine) in dogs with spontaneous neoplasia. J Vet Intern Med. 2004 Jul-Aug;18(4):536-9.

[4]. Pierro JA, et al. Phase I clinical trial of vinorelbine in tumor-bearing cats. J Vet Intern Med. 2013 Jul-Aug;27(4):943-8.
Density 1.36g/cm3
Melting Point 181-183°C
Molecular Formula C53H66N4O20
Molecular Weight 1079.106
Exact Mass 1078.427002
PSA 363.99000
LogP 0.44920
Index of Refraction 1.675
Storage condition 2-8°C
Water Solubility H2O: 10 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RD2535000
CAS REGISTRY NUMBER :
125317-39-7
LAST UPDATED :
199706
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C45-H54-N4-O8.2C4-H6-O6
MOLECULAR WEIGHT :
1079.23

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
2 mg/kg
SEX/DURATION :
female 7-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 27,1375,1993
Hazard Codes Xi:Irritant
Risk Phrases R43
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2942000000
HS Code 2942000000

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title: CAS No. 125317-39-7 | Chemsrc address: https://www.chemsrc.com/en/baike/828709.html

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