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162652-95-1

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  • Aspidospermidine-3-carboxylicacid,4-(acetyloxy)-6,7-didehydro-15-[(2R,4R,6S,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-1

    Cas No: 162652-95-1

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162652-95-1 Usage

Description

Vinflunine (also referred to as PM391) is a semisynthetic analog of the natural vinca alkaloids vinblastine and vincristine that was approved by the European Medicines Agency (EMEA) in 2009 for the treatment of adult patients with advanced or metastatic transitional cell carcinoma of the urothelial tract after failure of a prior platinum-containing regimen. Vinflunine is synthesized from anhydrovinblastine in a superacid media (HF-SbF5) and in the presence of a chlorinated solvent like CHCl3 or CCl4.

Originator

Pierre Fabre (France)

Definition

ChEBI: An organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethy group attached to this ring has been replaced by a 1,1-difluoroethyl group.

Brand name

Javlor

Clinical Use

Antineoplastic agent (vinca alkaloid): Treatment of advanced or metastatic bladder cancer

Drug interactions

Potentially hazardous interactions with other drugs Antibacterials: possible increased risk of ventricular arrhythmias with delamanid; concentration possibly reduced by rifampicin - avoid. Antidepressants: concentration possibly reduced by St Johns wort - avoid. Antifungals: concentration increased by ketoconazole and possibly itraconazole (increased risk of neurotoxicity) - avoid. Antimalarials: avoid with piperaquine with artenimol. Antipsychotics: avoid with clozapine (increased risk of agranulocytosis). Antivirals: concentration possibly increased by ritonavir - avoid. Grapefruit juice: concentration of vinflunine increased - avoid.

Metabolism

Metabolised by the cytochrome CYP3A4 isoenzyme, except for 4-O-deacetylvinflunine (DVFL), the only active metabolite and main metabolite in blood which is formed by multiple esterases. Excretion occurs via the faeces (about two-thirds) and the urine (about one-third).

Check Digit Verification of cas no

The CAS Registry Mumber 162652-95-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,2,6,5 and 2 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 162652-95:
(8*1)+(7*6)+(6*2)+(5*6)+(4*5)+(3*2)+(2*9)+(1*5)=141
141 % 10 = 1
So 162652-95-1 is a valid CAS Registry Number.
InChI:InChI=1/C45H54F2N4O8/c1-8-42-14-11-16-51-17-15-43(36(42)51)30-19-31(34(56-5)20-33(30)49(4)37(43)45(55,40(54)58-7)38(42)59-25(2)52)44(39(53)57-6)21-26-18-27(41(3,46)47)23-50(22-26)24-29-28-12-9-10-13-32(28)48-35(29)44/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3/t26-,27-,36-,37+,38+,42+,43+,44-,45-/m0/s1

162652-95-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Vinflunine

1.2 Other means of identification

Product number -
Other names C'-Norvincaleukoblastine,4'-deoxy-20',20'-difluoro

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:162652-95-1 SDS

162652-95-1Synthetic route

vinorelbine
71486-22-1

vinorelbine

vinflunine
162652-95-1

vinflunine

Conditions
ConditionsYield
With tetrachloromethane; hydrogen fluoride; antimony pentafluoride at -40℃;35%
vinflunine
162652-95-1

vinflunine

C45H53F2IN4O8
1007315-28-7

C45H53F2IN4O8

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid In dichloromethane at -15℃; for 1h;94%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

vinflunine
162652-95-1

vinflunine

vinflunine para-toluene sulfonate

vinflunine para-toluene sulfonate

Conditions
ConditionsYield
In ethyl acetate; acetone
benzoic acid
65-85-0

benzoic acid

vinflunine
162652-95-1

vinflunine

vinflunine benzoate

vinflunine benzoate

Conditions
ConditionsYield
In ethyl acetate
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

vinflunine
162652-95-1

vinflunine

vinflunine fumarate
1046795-80-5

vinflunine fumarate

Conditions
ConditionsYield
In methanol; acetone
(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

vinflunine
162652-95-1

vinflunine

vinflunine mandelate
1046795-83-8

vinflunine mandelate

Conditions
ConditionsYield
In acetone
L-Lactic acid
79-33-4

L-Lactic acid

vinflunine
162652-95-1

vinflunine

vinflunine lactate

vinflunine lactate

Conditions
ConditionsYield
In acetone
vinflunine
162652-95-1

vinflunine

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

vinflunine para-hydroxy-benzoate
1046795-84-9

vinflunine para-hydroxy-benzoate

Conditions
ConditionsYield
In acetone
vinflunine
162652-95-1

vinflunine

vinflunine hydrobromide

vinflunine hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In water; acetone
vinflunine
162652-95-1

vinflunine

vinflunine sulfate
162809-05-4

vinflunine sulfate

Conditions
ConditionsYield
With sulfuric acid In ethanol; water; acetone
trifluoroacetic acid
76-05-1

trifluoroacetic acid

vinflunine
162652-95-1

vinflunine

C46H54F2N4O9
1007315-29-8

C46H54F2N4O9

Conditions
ConditionsYield
With hexamethylenetetramine at 75℃; for 1h;
vinflunine
162652-95-1

vinflunine

desacetylvinflunine hydrazide
1454288-51-7

desacetylvinflunine hydrazide

Conditions
ConditionsYield
With hydrazine In methanol at 60℃;

162652-95-1Upstream product

162652-95-1Relevant articles and documents

Vinca alkaloids in superacidic media: A method for creating a new family of antitumor derivatives

Fahy,Duflos,Ribet,Jacquesy,Berrier,Jouannetaud,Zunino

, p. 8576 - 8577 (2007/10/03)

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