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MedKoo Cat#: 597629 | Name: Ambamustine HCl

Description:

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

Ambamustine, also known as PTT-119, is a novel tripeptide anticancer agent. PTT 119 was demonstrated to have antileukemic activity on murine and human cell lines. Most leukemic cell populations appeared to be responsive to the drug in a dose-related fashion. By cluster analysis, it was possible to discriminate subsets of samples according to PTT 119 sensitivity, and to investigate cross resistance with cytosine arabinoside and daunorubicin. PTT 119 may deserve applications in the treatment of acute nonlymphoblastic leukemia patients.

Chemical Structure

Ambamustine HCl
Ambamustine HCl
CAS#83996-50-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 597629

Name: Ambamustine HCl

CAS#: 83996-50-3 (HCl)

Chemical Formula: C29H40Cl3FN4O4S

Exact Mass:

Molecular Weight: 666.07

Elemental Analysis: C, 52.29; H, 6.05; Cl, 15.97; F, 2.85; N, 8.41; O, 9.61; S, 4.81

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 #
85754-59-2 (free base) 83996-50-3 (HCl)
Synonym
Ambamustine hydrochloride; Ambamustine HCl; PT 119; PT-119; PT119; PTT-119; PTT 119; PTT119;
IUPAC/Chemical Name
ethyl ((S)-2-((S)-2-amino-3-(4-fluorophenyl)propanamido)-3-(3-(bis(2-chloroethyl)amino)phenyl)propanoyl)-L-methioninate hydrochloride
InChi Key
LPRJQYQONDUPFK-OUKLVGRUSA-N
InChi Code
InChI=1S/C29H39Cl2FN4O4S.ClH/c1-3-40-29(39)25(11-16-41-2)34-28(38)26(35-27(37)24(33)18-20-7-9-22(32)10-8-20)19-21-5-4-6-23(17-21)36(14-12-30)15-13-31;/h4-10,17,24-26H,3,11-16,18-19,33H2,1-2H3,(H,34,38)(H,35,37);1H/t24-,25-,26-;/m0./s1
SMILES Code
CSCC[C@@H](C(OCC)=O)NC([C@H](CC1=CC=CC(N(CCCl)CCCl)=C1)NC([C@H](CC2=CC=C(F)C=C2)N)=O)=O.[H]Cl
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 666.07 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: Ardizzoni A, Antonelli G, Ricci S, Frasci G, Rinaldi M, Boni L, Galletti P, Pennucci MC, Antonuzzo A, Gravina A, Galli L, Comella G, Conte PF, Salvati F, Rosso R. Ambamustine in the second-line treatment of patients with small-cell lung cancer: a phase II Fonicap study. Am J Clin Oncol. 2000 Feb;23(1):22-5. PubMed PMID: 10683068. 2: Manna A, Porcellini A, Visani G, Marchetti-Rossi MT, Tura S. Limiting dilution analysis of a novel tripeptide anticancer agent Ambamustine (PTT-119): effect on K-562, CCRF-SB and multidrug resistant LoVo-Dk cell lines. Exp Hematol. 1994 Jun;22(6):517-20. PubMed PMID: 8187848. 3: Ambamustine. PTT119. Drugs R D. 2003;4(2):119-21. PubMed PMID: 12718568. 4: Mattii L, Barale R, Petrini M. Use of the comet test in the evaluation of multidrug resistance of human cell lines. Leukemia. 1998 Apr;12(4):627-32. PubMed PMID: 9557624. 5: Yagi MJ, Bekesi JG. Differential susceptibility and cytopathic alterations induced by PTT. 119, a new cancericidal compound, p-fluoro-Phe-L-Phe-m-bis-(2-chloroethyl)amino-L-Phe-Met ethoxy HCl. Biomed Pharmacother. 1983;37(7):329-38. PubMed PMID: 6667339. 6: Coppi G, Mosconi P, Gatti T, Berti MA. Toxicological aspects of a new tripeptide mustard. Farmaco Prat. 1985 Jul;40(7):242-52. PubMed PMID: 4029370. 7: Dubini F, Sezzano P, Berti MA, Coppi G. Mutagenicity studies on PTT-119. Farmaco Prat. 1987 Oct;42(10):269-79. PubMed PMID: 3322876. 8: Coppi G, Berti MA, Gatti T, Mosconi P. Some pharmacological studies on a new tripeptide mustard. Farmaco Sci. 1984 Jan;39(1):26-34. PubMed PMID: 6705911. 9: Houghton PJ, Tharp R, Houghton JA, Holland JF, Bekesi JG. Evaluation of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis-(2-chloroethyl) aminophenyl]-L-alanyl-L-methionine ethyl ester HCl (PTT.119) against xenografts of human rhabdomyosarcoma. Cancer Chemother Pharmacol. 1988;22(3):201-4. PubMed PMID: 3409455. 10: Visani G, Lemoli RM, Tosi P, Verlicchi F, Gamberi B, Cenacchi AR, Colombini R, Fogli M, Russo D, Zuffa E, et al. Sensitivity of chronic myeloid leukemia hemopoietic progenitors to PTT-119 in combination with human recombinant interferon alpha and gamma. Blut. 1990 May;60(5):287-90. PubMed PMID: 2112414. 11: Pannuti F, Coppi G, Borella F, Martoni A, Urbano L, Melotti B. Pharmacokinetics of PTT-119 in man. Chemioterapia. 1988 Apr;7(2):113-6. PubMed PMID: 3396115. 12: Tura S, Mazza P, Gherlinzoni F, Zinzani PL, Poletti G, Visani G, Lemoli RM, Bandini G, Cavo M, Galieni P, et al. Phase II study with a new alkylating agent (PTT-119) in lymphoid malignancies. Haematologica. 1988 Nov-Dec;73(6):503-8. PubMed PMID: 3148513. 13: Lemoli RM, Visani G, Tosi P, Mazza P, Motta MR, Rizzi S, Zinzani PL, Poluzzi C, Gherlinzoni F, Tura S. Effects of a new bifunctional alkylating agent (PTT-119) on in vitro growth of human cell lines and normal myeloid progenitors (CFU-GM). Haematologica. 1988 May-Jun;73(3):195-200. PubMed PMID: 3139515. 14: De Barbieri A, Dall'Asta L, Comini A, Springolo V, Mosconi P, Coppi G. Synthesis, acute toxicity and chemotherapeutic anti-cancer activities of a new tripeptidic mustard. Farmaco Sci. 1983 Apr;38(4):205-18. PubMed PMID: 6861998. 15: Bianchi R, Nardelli B, Allegrucci M, Fioretti MC. [Therapeutic effectiveness of PTT-119 evaluated in vivo in experimental models]. G Ital Chemioter. 1985 Jan-Apr;32(1):1-6. Italian. PubMed PMID: 3830770. 16: Roboz J, Greaves J, Yagi MJ, Holland JF, Bekesi JG. Analytical and pharmacological studies on a new antineoplastic tripeptide, PTT.119. Pharmacology. 1985;30(1):52-9. PubMed PMID: 3975256. 17: Dal Pozzo O, Santini V, Saccardi R, Bernabei PA, Rossi Ferrini P. Assessment of PTT 119 activity on acute nonlymphoblastic leukemia cells by [3H]-thymidine uptake inhibition and cluster analysis. Haematologica. 1990 Jan-Feb;75(1):50-3. PubMed PMID: 2338287. 18: Verlicchi F, Boschi S, Visani G, Guidi A, Tosi P, Cavo M, Tura S. Evidence for increased intracellular transport of m-sarcolysine (alkylating moiety) when combined with two amino acid analogs (PTT-119). Blut. 1990 Nov;61(5):311-3. PubMed PMID: 2271778. 19: Tura S, Mazza P, Gherlinzoni F, Zinzani PL, Poletti G, Visani G, Lemoli RM, Cavo M, Galieni P, Tassi C, et al. Phase II study of a new alkylating agent (PTT-119) in resistant-relapsed non-Hodgkin's lymphomas. Cancer Chemother Pharmacol. 1989;23(2):123-5. PubMed PMID: 2910510. 20: Yagi MJ, Zanjani M, Holland JF, Bekesi JG. Increased cancericidal activity of PTT.119; a new synthetic bis-(2-chloroethyl)amino-L-phenylalanine derivative with carrier amino acids. II. In vivo bioassay. Cancer Chemother Pharmacol. 1984;12(2):77-82. PubMed PMID: 6697428.