MedKoo Cat#: 585301 | Name: Carzelesin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Carzelesin is an antitumor agent.

Chemical Structure

Carzelesin
Carzelesin
CAS#119813-10-4

Theoretical Analysis

MedKoo Cat#: 585301

Name: Carzelesin

CAS#: 119813-10-4

Chemical Formula: C41H37ClN6O5

Exact Mass: 728.2514

Molecular Weight: 729.23

Elemental Analysis: C, 67.53; H, 5.11; Cl, 4.86; N, 11.52; O, 10.97

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Carzelesin; U 80244; U-80244; U80244
IUPAC/Chemical Name
[(8S)-8-(chloromethyl)-6-[5-[[6-(diethylamino)-1-benzofuran-2-carbonyl]amino]-1H-indole-2-carbonyl]-1-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indol-4-yl] N-phenylcarbamate
InChi Key
BBZDXMBRAFTCAA-AREMUKBSSA-N
InChi Code
InChI=1S/C41H37ClN6O5/c1-4-47(5-2)29-13-11-24-17-35(52-33(24)18-29)39(49)44-28-12-14-30-25(15-28)16-31(46-30)40(50)48-22-26(20-42)37-32(48)19-34(38-36(37)23(3)21-43-38)53-41(51)45-27-9-7-6-8-10-27/h6-19,21,26,43,46H,4-5,20,22H2,1-3H3,(H,44,49)(H,45,51)/t26-/m1/s1
SMILES Code
O=C(OC1=CC(N(C(C(N2)=CC3=C2C=CC(NC(C(O4)=CC5=C4C=C(N(CC)CC)C=C5)=O)=C3)=O)C[C@H]6CCl)=C6C7=C1NC=C7C)NC8=CC=CC=C8
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 729.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wolff I, Bench K, Beijnen JH, Bruntsch U, Cavalli F, de Jong J, Groot Y, van Tellingen O, Wanders J, Sessa C. Phase I clinical and pharmacokinetic study of carzelesin (U-80244) given daily for five consecutive days. Clin Cancer Res. 1996 Oct;2(10):1717-23. PubMed PMID: 9816122. 2: Pavlidis N, Aamdal S, Awada A, Calvert H, Fumoleau P, Sorio R, Punt C, Verweij J, van Oosterom A, Morant R, Wanders J, Hanauske AR. Carzelesin phase II study in advanced breast, ovarian, colorectal, gastric, head and neck cancer, non-Hodgkin's lymphoma and malignant melanoma: a study of the EORTC early clinical studies group (ECSG). Cancer Chemother Pharmacol. 2000;46(2):167-71. PubMed PMID: 10972487. 3: Jonkman-De Vries JD, Rosing H, Henrar RE, Bult A, Beijnen JH. The influence of formulation excipients on the stability of the novel antitumor agent carzelesin (U-80,244). PDA J Pharm Sci Technol. 1995 Nov-Dec;49(6):283-8. PubMed PMID: 8581459. 4: Li LH, DeKoning TF, Kelly RC, Krueger WC, McGovren JP, Padbury GE, Petzold GL, Wallace TL, Ouding RJ, Prairie MD, et al. Cytotoxicity and antitumor activity of carzelesin, a prodrug cyclopropylpyrroloindole analogue. Cancer Res. 1992 Sep 15;52(18):4904-13. PubMed PMID: 1516047. 5: van Tellingen O, Punt CJ, Awada A, Wagener DJ, Piccart MJ, Groot Y, Schaaf LJ, Henrar RE, Nooijen WJ, Beijnen JH. A clinical pharmacokinetics study of carzelesin given by short-term intravenous infusion in a phase I study. Cancer Chemother Pharmacol. 1998;41(5):377-84. PubMed PMID: 9523733. 6: van Tellingen O, Nooijen WJ, Schaaf LJ, van der Valk M, van Asperen J, Henrar RE, Beijnen JH. Comparative pharmacology of the novel cyclopropylpyrroloindole-prodrug carzelesin in mice, rats, and humans. Cancer Res. 1998 Jun 1;58(11):2410-6. PubMed PMID: 9622082. 7: Awada A, Punt CJ, Piccart MJ, Van Tellingen O, Van Manen L, Kerger J, Groot Y, Wanders J, Verweij J, Wagener DJ. Phase I study of Carzelesin (U-80,244) given (4-weekly) by intravenous bolus schedule. Br J Cancer. 1999 Mar;79(9-10):1454-61. PubMed PMID: 10188890; PubMed Central PMCID: PMC2362731. 8: Houghton PJ, Cheshire PJ, Hallman JD 2nd, Houghton JA. Therapeutic efficacy of the cyclopropylpyrroloindole, carzelesin, against xenografts derived from adult and childhood solid tumors. Cancer Chemother Pharmacol. 1995;36(1):45-52. PubMed PMID: 7720175. 9: Hidalgo M, Izbicka E, Cerna C, Gomez L, Rowinsky EK, Weitman SD, Von Hoff DD. Comparative activity of the cyclopropylpyrroloindole compounds adozelesin, bizelesin and carzelesin in a human tumor colony-forming assay. Anticancer Drugs. 1999 Mar;10(3):295-302. PubMed PMID: 10327036. 10: Vries JD, Doppenberg WG, Henrar RE, Bult A, Beijnen JH. Systematic study on the chemical stability of the prodrug antitumor agent carzelesin (U-80,244). J Pharm Sci. 1996 Nov;85(11):1227-33. PubMed PMID: 8923330. 11: Yoon JH, Lee CS. Sequence selectivity of DNA alkylation by adozelesin and carzelesin. Arch Pharm Res. 1998 Aug;21(4):385-90. PubMed PMID: 9875464. 12: van Tellingen O, Pels EM, Henrar RE, Schaaf LJ, Padbury GE, Beijnen JH, Nooijen WJ. Fully automated high-performance liquid chromatographic method for the determination of carzelesin (U-80,244) and metabolites (U-76,073 and U-76,074) in human plasma. J Chromatogr. 1994 Jan 14;652(1):51-8. PubMed PMID: 8014227. 13: Filippini C, Bisiach M, Tagliabue G, D'Incalci M, Ubezio P. Hematopoietic toxicity and cell cycle perturbations induced by new DNA minor groove-alkylating agents. Int J Cancer. 1997 Sep 4;72(5):801-9. PubMed PMID: 9311597. 14: Jonkman-de Vries JD, de Graaff-Teulen MJ, Henrar RE, Kettenes-van den Bosch JJ, Bult A, Beijnen JH. Pharmaceutical development of a parenteral formulation of the novel anti-tumor agent carzelesin (U-80,244). Invest New Drugs. 1994;12(4):303-14. PubMed PMID: 7775131. 15: Reddy BS, Sondhi SM, Lown JW. Synthetic DNA minor groove-binding drugs. Pharmacol Ther. 1999 Oct;84(1):1-111. Review. PubMed PMID: 10580832. 16: Workman P, Kaye SB, Schwartsmann G. Laboratory and phase I studies of new cancer drugs. Curr Opin Oncol. 1992 Dec;4(6):1065-72. Review. Erratum in: Curr Opin Oncol 1993 Mar;5(2):434. PubMed PMID: 1360819. 17: Ghielmini M, Bosshard G, Capolongo L, Geroni MC, Pesenti E, Torri V, D'Incalci M, Cavalli F, Sessa C. Estimation of the haematological toxicity of minor groove alkylators using tests on human cord blood cells. Br J Cancer. 1997;75(6):878-83. PubMed PMID: 9062410; PubMed Central PMCID: PMC2063413. 18: Verweij J. New promising anticancer agents in development: what comes next? Cancer Chemother Pharmacol. 1996;38 Suppl:S3-10. Review. PubMed PMID: 8765408. 19: Bergon M. Comments on 'Systematic study on the chemical stability of the prodrug antitumor agent carzelesin (U-80,244)'. J Pharm Sci. 1997 Sep;86(9):1070-1. PubMed PMID: 9294825. 20: Denny WA. DNA minor groove alkylating agents. Curr Med Chem. 2001 Apr;8(5):533-44. Review. PubMed PMID: 11281840.