Alanosine
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MedKoo CAT#: 200130

CAS#: 5854-93-3

Description: Alanosine, also known as L-alanosine, is an amino acid analogue and antibiotic derived from the bacterium Streptomyces alanosinicus with antimetabolite and potential antineoplastic activities. L-alanosine inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate, an intermediate in purine metabolism. L-alanosine-induced disruption of de novo purine biosynthesis is potentiated by methylthioadenosine phosphorylase (MTAP) deficiency. The clinical use of this agent may be limited by its toxicity profile. MTAP is a key enzyme in the adenine and methionine salvage pathways.


Chemical Structure

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Alanosine
CAS# 5854-93-3

Theoretical Analysis

MedKoo Cat#: 200130
Name: Alanosine
CAS#: 5854-93-3
Chemical Formula: C3H7N3O4
Exact Mass: 149.04366
Molecular Weight: 149.11
Elemental Analysis: C, 24.17; H, 4.73; N, 28.18; O, 42.92

Size Price Shipping out time Quantity
10mg USD 190 Same Day
25mg USD 350 Same Day
50mg USD 550 Same Day
100mg USD 950 Same Day
200mg USD 1450 Same Day
500mg USD 2950 Same Day
1g USD 3850 Same Day
Inquire bulk and customized quantity

Pricing updated 2021-03-08. Prices are subject to change without notice.

Alanosine, purity > 98%, is in stock. The same day shipping out after order is received.

Synonym: SDX102; SDX-102; SDX 102; alanosine; L-alanosine.

IUPAC/Chemical Name: (S)-2-amino-3-(hydroxy(nitroso)amino)propanoic acid

InChi Key: MLFKVJCWGUZWNV-REOHCLBHSA-N

InChi Code: InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,10H,1,4H2,(H,7,8)/t2-/m0/s1

SMILES Code: O=C(O)[C@@H](N)CN(O)N=O

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 water

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 149.11 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Kindler HL, Burris HA 3rd, Sandler AB, Oliff IA. A phase II multicenter study of L-alanosine, a potent inhibitor of adenine biosynthesis, in patients with MTAP-deficient cancer. Invest New Drugs. 2009 Feb;27(1):75-81. doi: 10.1007/s10637-008-9160-1. Epub 2008 Jul 11. PubMed PMID: 18618081.

2: Li XM, Kanekal S, Crépin D, Guettier C, Carrière J, Elliott G, Lévi F. Circadian pharmacology of L-alanosine (SDX-102) in mice. Mol Cancer Ther. 2006 Feb;5(2):337-46. PubMed PMID: 16505107.

3: Huang J, Lipscomb WN. T-state active site of aspartate transcarbamylase: crystal structure of the carbamyl phosphate and L-alanosine ligated enzyme. Biochemistry. 2006 Jan 17;45(2):346-52. PubMed PMID: 16401065.

4: Batova A, Cottam H, Yu J, Diccianni MB, Carrera CJ, Yu AL. EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine. Blood. 2006 Feb 1;107(3):898-903. Epub 2005 Oct 18. PubMed PMID: 16234352; PubMed Central PMCID: PMC1895892.

5: Li W, Su D, Mizobuchi H, Martin DS, Gu B, Gorlick R, Cole P, Bertino JR. Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells. Oncol Res. 2004;14(7-8):373-9. PubMed PMID: 15301428.

6: Gantverg A, Elliott G, Pineault J, Demers R. Determination of derivatized l-alanosine in plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Apr 25;803(2):311-5. PubMed PMID: 15063341.

7: Efferth T, Gebhart E, Ross DD, Sauerbrey A. Identification of gene expression profiles predicting tumor cell response to L-alanosine. Biochem Pharmacol. 2003 Aug 15;66(4):613-21. PubMed PMID: 12906926.

8: Yu J. Alanosine (UCSD). Curr Opin Investig Drugs. 2001 Nov;2(11):1623-30. Review. PubMed PMID: 11763167.

9: Batova A, Diccianni MB, Omura-Minamisawa M, Yu J, Carrera CJ, Bridgeman LJ, Kung FH, Pullen J, Amylon MD, Yu AL. Use of alanosine as a methylthioadenosine phosphorylase-selective therapy for T-cell acute lymphoblastic leukemia in vitro. Cancer Res. 1999 Apr 1;59(7):1492-7. PubMed PMID: 10197619.

10: Guicherit OM, Cooper BF, Rudolph FB, Kellems RE. Amplification of an adenylosuccinate synthetase gene in alanosine-resistant murine T-lymphoma cells. Molecular cloning of a cDNA encoding the "non-muscle" isozyme. J Biol Chem. 1994 Feb 11;269(6):4488-96. PubMed PMID: 8308018.



Additional Information