3-O-Demethylfortimicin A

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

MedKoo CAT#: 571132

CAS#: 74842-47-0

Description: 3-O-Demethylfortimicin A is an antibiotic.


Price and Availability

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3-O-Demethylfortimicin A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571132
Name: 3-O-Demethylfortimicin A
CAS#: 74842-47-0
Chemical Formula: C16H33N5O6
Exact Mass: 391.2431
Molecular Weight: 391.47
Elemental Analysis: C, 49.09; H, 8.50; N, 17.89; O, 24.52


Synonym: 3-O-Demethylfortimicin A; A49759; A-49759; A 49759

IUPAC/Chemical Name: 2-amino-N-((1R,2R,3R,4S,5R,6S)-4-amino-3-(((2R,3R,6R)-3-amino-6-((R)-1-aminoethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,5,6-trihydroxycyclohexyl)-N-methylacetamide

InChi Key: InChI=1S/C16H33N5O6/c1-6(18)8-4-3-7(19)16(26-8)27-15-10(20)12(23)13(24)11(14(15)25)21(2)9(22)5-17/h6-8,10-16,23-25H,3-5,17-20H2,1-2H3/t6-,7-,8-,10+,11-,12-,13+,14-,15-,16-/m1/s1

InChi Code: InChI=1S/C16H33N5O6/c1-6(18)8-4-3-7(19)16(26-8)27-15-10(20)12(23)13(24)11(14(15)25)21(2)9(22)5-17/h6-8,10-16,23-25H,3-5,17-20H2,1-2H3/t6-,7-,8-,10+,11-,12-,13+,14-,15-,16-/m1/s1

SMILES Code: C[C@@H](N)[C@H](O1)CC[C@@H](N)[C@H]1O[C@@H]([C@@H]2O)[C@@H](N)[C@@H](O)[C@@H](O)[C@H]2N(C(CN)=O)C


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Sennello LT, Wilson DS, Afarian J, Holtam LS, Norman G, Rollins DE, Tolman KG. Single-dose pharmacokinetics of 3-O-demethylfortimicin A in humans after intravenous and intramuscular administration. Antimicrob Agents Chemother. 1986 Mar;29(3):400-4. PubMed PMID: 3717941; PubMed Central PMCID: PMC180402.

2: Tadanier J, Hallas R. 3-O-demethyl-2,3-di-epi-fortimicins and 3-O-demethyl-3-epi-fortimicins. J Antibiot (Tokyo). 1983 Mar;36(3):256-66. PubMed PMID: 6833145.

3: Neu HC. The in-vitro activity of O-demethylfortimicin. J Antimicrob Chemother. 1983 Feb;11(2):181-5. PubMed PMID: 6833173.

4: Jones RN, Thornsberry C, Barry AL, Packer RR, Baker CN, Badal RE. Compound A49759, the 3-O-demethyl derivative of fortimicin A: in vitro comparison with six other aminoglycoside antibiotics. Antimicrob Agents Chemother. 1980 Nov;18(5):773-9. PubMed PMID: 7447431; PubMed Central PMCID: PMC284090.

5: Kimura ET, Tekeli S, Pratt MC, Kesterson JW, Cusick PK, Heyman IA, Majors KR. Acute, subchronic, and chronic toxicity studies with 3-O demethylfortimicin A disulfate, a new aminocyclitol antibiotic. Toxicol Appl Pharmacol. 1985 Aug;80(1):66-77. PubMed PMID: 4024109.

6: Yang CL, Tekeli S, Lehrer SB, Cusick PK, Kesterson JW. Comparative vestibular toxicity study with 3-O-demethylfortimicin A disulfate and gentamicin sulfate in cats. Drug Chem Toxicol. 1987;10(3-4):237-56. PubMed PMID: 3501364.

7: Barry AL, Jones RN, Thornsberry C, Gavan TL, Gerlach EH, Sommer HM.
3-0-demethyl fortimicin A: in vitro activity and interpretive zone standards for disk diffusion susceptibility tests. Eur J Clin Microbiol. 1984 Dec;3(6):531-7. PubMed PMID: 6441709.

8: Serieys C, Bergogne-Bérézin E, Prokocimer P, Delcercq D. [Clinical and
bacteriological study of O-demethylfortimicin A sulfate in urinary infection]. Pathol Biol (Paris). 1986 May;34(5):490-3. French. PubMed PMID: 3534728.

9: Girolami RL, Stamm JM. Comparative antimicrobial activity of O-demethylfortimicin A, a derivative of fortimicin A. Antimicrob Agents Chemother. 1980 Nov;18(5):766-72. PubMed PMID: 7447430; PubMed Central PMCID: PMC284089.

10: Lartey PA, Grampovnik DJ. The base catalyzed rearrangement of
3-O-demethylfortimicin A. J Antibiot (Tokyo). 1980 Sep;33(9):1071-3. PubMed PMID: 7440411.

11: Martin JR, Johnson P, Tadanier J, Goldstein A. Synthesis of 3-O-demethylfortimicins. Antimicrob Agents Chemother. 1980 Nov;18(5):761-5. PubMed PMID: 6778386; PubMed Central PMCID: PMC284088.