Vindesine

HCID 40839CAS 53643-48-4

기본 정보

표준 SMILES
CC[C@]1(O)C[C@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(N)=O)[C@H](O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1
InChIKey
HHJUWIANJFBDHT-KOTLKJBCSA-N
분자식
C43H55N5O7
평균 분자량
753.9 g/mol
단동위원소 질량
753.4101491

개요

Vindesine is a primary carboxamide, a methyl ester, a tertiary alcohol, a vinca alkaloid, an organic heterotetracyclic compound, an organic heteropentacyclic compound and a tertiary amino compound. It has a role as an antineoplastic agent. It is functionally related to a vincaleukoblastine.

이름 및 식별자

우선 이름
Vindesine
IUPAC
methyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

이름 및 동의어

vindesine53643-48-4Desacetylvinblastine amideVindesinumVincaleukoblastine, 3-(aminocarbonyl)-O4-deacetyl-3-de(methoxycarbonyl)-DTXSID6023739VindesinCHEBI:363733-(aminocarbonyl)-O(4)-deacetyl-3-de(methoxycarbonyl)vincaleukoblastineCompound 112531methyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylatevindesin sulfate
이름 더 보기
vindesin sulphatemethyl (13S,15S,17S)-13-((1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo(10.6.1.0^(1,9).0^(2,7).0^(16,19))nonadeca-2(7),3,5,13-tetraen-4-yl)-17-ethyl-17-hydroxy-1,11-diazatetracyclo(13.3.1.0^(4,12).0^(5,10))nonadeca-4(12),5,7,9-tetraene-13-carboxylatemethyl (13S,15S,17S)-13-((1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,13-tetraen-4-yl)-17-ethyl-17-hydroxy-1,11-diazatetracyclo(13.3.1.04,12.05,10)nonadeca-4(12),5,7,9-tetraene-13-carboxylatemethyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylateLilly CT-3231RefChem:901872Deacetylvinblastine CarboxamideDTXCID203739

데이터베이스 식별자

CAS
53643-48-4、59917-39-4
PubChem CID
40839
DTXSID
DTXSID6023739
ChEMBL
CHEMBL238071
ChEBI
CHEBI:36373
EC Number
258-682-2
Nikkaji
J24.547J

물성

구조 계산 물성

XLogP
2.7
극성 표면적
165 Ų
수소 결합 공여자 수
5
수소 결합 수용자 수
10
회전 가능 결합 수
7
무거운 원자 수
55

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP2.9
Color/FormCrystal from ethanol-methanol
Solubility7.00e-02 g/L
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 3건

230-232 °C

230-232 °C

230 - 232 °C

안전 및 규제

안전 및 보호

Storage ConditionsIntact vials should be refrigerated at 2-8 °C. The constituted soln is stable under refrigeration for 30 days. /Vindesine sulfate/
Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

독성 정보

Treatment · 1건

Activated charcoal binds most toxic agents and can decrease their systemic absorption if administered soon after ingestion. Immediate dilution with milk or water may be of benefit in caustic or irritant chemical ingestions. If the exposure occurred through inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. in case of acute lung injury, Maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (T36)

Interactions · 5건

Leukopenic and/or thrombocytopenic effects of vindesine may be increased with concurrent or recent therapy if these medications /blood dyscrasia causing medications/ cause the same effects; dosage adjustment of vindesine, if necessary, should be based on blood counts.

Additive bone marrow depression, including severe dermatitis and/or mucositis, may occur; dosage reduction may be required when two or more bone marrow depressants, including radiation, are used concurrently or consecutively.

Acute shortness of breath and severe bronchospasm have frequently been reported with combination therapy including vinca alkaloids; the reaction may occur within minutes or several hours after the vinca alkaloid is injected.

Neurologic toxicity may occur early in treatment and may be more severe if used concomitantly with other drugs having a neurotoxic potential.

For more Interactions (Complete) data for VINDESINE (7 total), please visit the HSDB record page.

Health EffectsThe bone marrow depressant effects of vindesine may result in an increased incidence of microbial infection, delayed healing, and gingival bleeding (A609).
Exposure RoutesIngestion, inhalation (T36, A566).
Toxicity SummaryVindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. The drug is cell-cycle specific for the S phase.
Human Toxicity Excerpts · 3건

Overdose (45 mg instead of 4.5 mg) leads to generalized muscle pain, tinnitus, diarrhea, sleeplessness, burning sensation in mouth, & hiccups. Patients usually respond to supportive treatment (parenteral nutritional leucovortin, citruline 600 mg/day, arginine 1200 mg/day, & ornithine 600 mg/day).

Neurotoxicity forms a major limitation in many clinical applications of vincristine and other powerful vinca alkaloid anticancer drugs. Using the nerve growth factor (NGF) dependent neurite outgrowth from the PC12 pheochromocytoma cell line as an in vitro assay for neurotoxicity, the effect of different concentrations of vincristine (0.55; 1.1 and 11 nM) was compared with that of vindesine and vinblastine. Vincristine in comparatively low concentration (0.55 nM) could significantly decrease the percentage of neurite forming cells from 74% to 32% within a three day incubation period. Especially the longer neurites (> 2 x cell body) proved to be extremely sensitive for vincristine effects. Vinblastine and vindesine were also able to decrease, dose dependently and significantly, the percentage of neurite forming cells. However, the effects observed were less severe than that of vincristine. The sequentially increasing level of neurotoxicity due to vinblastine, vindesine and vincristine, as observed in the neurite outgrowth inhibition correlates well with previous findings from animal models and with data from the clinical practice. Withdrawal of vincristine resulted in a rapid restoration of neurite formation, suggesting the potential reversibility of neurotoxic effects in these cells. These results provide a validation of the PC12 neurite outgrowth assay as a suitable and reliable model for predicting neurotoxicity.

... Oncoprotein 18 (op18) was first isolated as a molecule overexpressed in several malignant cells, suggesting a function of op18 in malignant processes, such as differentiation in hematologic malignancies, op18 also was found to enhance microtubule deassembly in the cells. Antimitotic agents that bind to tubulin have been used for chemotherapy to treat solid tumors, such as lung carcinoma. Vinca alkaloids, such as vindesine and vincristine, have commonly been used for chemotherapy of nonsmall cell lung carcinoma. The authors examined the role of op18 in the sensitivity of human lung carcinoma cells to antimitotic agents. ... Expression of op18 mRNA was detected in all 17 lung carcinoma cell lines tested by Northern blotting. Oncoprotein 18 cDNA was transfected to SBC-3 human lung carcinoma cells, and the stable transfectants, SBC-3/op1-3, were isolated. The sensitivity of these transfectants against antimitotic agents were examined by the MTT assay in vitro. Cell cycle distribution of the transfectants on DNA histogram was analyzed by flow cytometry. ... Oncoprotein 18-transfected cells showed higher sensitivity to vindesine and vincristine, but not to taxanes. Vindesine-exposure increased the G2/M population of the cell cycle in the Mock transfectants, but not in SBC-3/op1, suggesting that the cell cycle dynamics were altered by op18 expression in SBC-3/op1. ... Oncoprotein 18 expression is associated with lung carcinoma cell sensitivity to vindesine and may be able to serve as a surrogate marker for the chemosensitivity to Vinca alkaloids in human lung carcinomas.

화학 및 산업

약리 정보

ATC Code · 3건

L01CA03

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein Binding65-75%
Pharmacodynamics · 1건

Vindesine is indicated for the treatment of acute lymphocytic leukemia of childhood that is resistant to vincristine and non-oat cell lung cancer. Vindesine causes the arrest of cells in metaphase mitosis. It is three times more potent than vincristine and nearly 10 times more potent than vinblastine in causing mitotic arrest in <i>in vitro</i> studies at doses designed to arrest from 10 to 15% of the cells in mitosis. Vindesine and vincristine are approximately equipotent at dose levels that arrest 40 to 50% of the cells in mitosis. Unlike vinblastine, vindesine produces very few postmetaphase cells. Vindesine has demonstrated activity in patients who have relapsed while receiving multiple-agent treatment that included vincristine.

Mechanism of Action · 2건

Vindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. The drug is cell-cycle specific for the S phase.

Vindesine causes the arrest of cells in metaphase mitosis. It is three times more potent than vincristine and nearly 10 times more potent than vinblastine in causing mitotic arrest in in vitro studies at doses designed to arrest from 10 to 15% of the cells in mitosis.Vindesine and vincristine are approximately equipotent at dose levels that arrest 40 to 50% of the cells in mitosis. Unlike vinblastine, vindesine produces very few postmetaphase cells.Vindesine has demonstrated activity in patients who have relapsed while receiving multiple-agent treatment that included vincristine. Toxic doses of vindesine given to male and female rats have not affected fertility.

Biological Half-Life24 hours.
Metabolism/Metabolites · 2건

Hepatic

Hepatic Half Life: 24 hours.

용도 및 제조

Uses · 2건

MEDICATION

Vindesine is used in chemotherapy to treat many different types of cancer, including leukaemia, lymphoma, melanoma, breast cancer, and lung cancer (L1022).

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