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Vinorelbine
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Name

Vinorelbine

 EINECS N/A
CAS No. 71486-22-1 Density 1.36 g/cm3
PSA 133.87000 LogP 4.69440
Solubility N/A Melting Point N/A
Formula C45H54N4O8 Boiling Point N/A
Molecular Weight 778.946 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 71486-22-1 (Vinorelbine) Hazard Symbols N/A
Synonyms

Vinorelbina [Spanish];Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-((2R,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, (2beta,3beta,4beta,5alpha,12beta,19alpha)-;Navelbine base;KW 2307 base;C-Norvincaleukoblastine, 3,4-didehydro-4-deoxy-;Aspidospermidine-3-carboxylic acid,4-(acetyloxy)-6,7-didehydro-15-[(2R,- 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,(2a,3a,4a,5R,12a,19R)-;Vinorelbinum [Latin];Vinorelbine bitartrate;Vinorelbine base;

Article Data 8

Vinorelbine Synthetic route

7693-46-1

4-Nitrophenyl chloroformate

71486-22-1

vinorelbine

C52H57N5O12

Conditions
ConditionsYield
With dmap In dichloromethane at 0℃; for 8h;83%
With dmap In dichloromethane at 0℃; for 8h;81%

3-(2-pyridyldithio)propylcarbamic acid-4-nitrophenyl ester

71486-22-1

vinorelbine

C52H62N6O8S2

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; Reflux;67.6%
71486-22-1

vinorelbine

C45H53IN4O8

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid In dichloromethane at -15℃;
71486-22-1

vinorelbine

C58H63N5O10S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap / dichloromethane / 8 h / 0 °C
2: dmap / dichloromethane / Reflux
View Scheme

Vinorelbine Specification

The Vinorelbine with CAS registry number of 71486-22-1 is also known as Vinorelbine bitartrate. The systematic name is C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-. It belongs to product categories of Active Pharmaceutical Ingredients; Antineoplastic. In addition, the formula is C45H54N4O8 and the molecular weight is 778.93.

Physical properties about Vinorelbine are: (1)ACD/LogP: 4.99; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 3.29; (4)ACD/LogD (pH 7.4): 4.86; (5)#H bond acceptors: 12; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 11; (8)Polar Surface Area: 133.87Å2; (9)Index of Refraction: 1.674; (10)Molar Refractivity: 214.19 cm3; (11)Molar Volume: 570.5 cm3; (12)Surface Tension: 68.7 dyne/cm; (13)Density: 1.36 g/cm3.

Preparation of Vinorelbine: it is prepared by reaction of anhydmvinblastine through two steps.

Vinorelbine is prepared by reaction of anhydmvinblastine through two steps.

Uses of Vinorelbine: it is used to produce C42H52N6O6. The reaction occurs with reagent NH2NH2 and solvent methanol at 60 °C. The yield is about 49%. Besides, it is approved for the treatment of Non small cell lung cancer and Metastatic breast cancer.

Vinorelbine is used to produce C42H52N6O6.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCC1=CC2CC(C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
2. Isomeric SMILES: CCC1=C[C@@H]2C[C@@](C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
3. InChI: InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)
54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37+,38-,39-,42-,43-,44+,45+/m1/s1
4. InChIKey: GBABOYUKABKIAF-JKVZWNDSSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 26mg/kg (26mg/kg)   Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 10, Pg. 1050, 1983.

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