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30562-34-6

30562-34-6 structure
30562-34-6 structure
  • Name: Geldanamycin
  • Chemical Name: geldanamycin
  • CAS Number: 30562-34-6
  • Molecular Formula: C29H40N2O9
  • Molecular Weight: 560.636
  • Catalog: API Antibiotics Other antibiotics
  • Create Date: 2018-06-09 11:11:06
  • Modify Date: 2025-08-22 11:28:41
  • Geldanamycin is a Hsp90 inhibitor with antimicrobial activity against many Gram-positive and some Gram-negative bacteria.
Name geldanamycin
Synonyms 2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-
GELDANAMYCIN,STREPTOMYCES HYGROSCOPICUS
Streptomyces hygroscopicus
GELDANAMYCIN FROM STRE
2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, (4Z,6Z,8S,9R,10Z,12R,14R,16R)-
(4Z,6Z,8S,9R,10Z,12R,14R,16R)-13-Hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
Geldanamycin
MFCD00274570
Geldanamycin from Streptomyces hygroscopicus
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-Hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
Geldanamycin (9CI)
Description Geldanamycin is a Hsp90 inhibitor with antimicrobial activity against many Gram-positive and some Gram-negative bacteria.
Related Catalog
Target

HSP90:1.2 μM (Kd)

In Vitro Geldanamycin significantly delays and reduces viperin expression, indicating that IRF3 is involved in viperin induction in RAW264.7 cells[1]. Geldanamycin (GA), a benzoquinone ansamycin, protected against neuronal injury induced by oxygen-glucose deprivation (OGD)/zVAD treatment in cultured primary neurons. More importantly, Geldanamycin decreases RIP1 protein level in a time and concentration-dependent manner. Geldanamycin also decreases the Hsp90 protein level, which causes instability of RIP1 protein, resulting in decreased RIP1 protein level but not RIP1 mRNA level after Geldanamycin treatment[2]. Geldanamycin (GA) is identified as the first natural product inhibitor of Hsp90 that binds to the N-terminal ATPase domain of Hsp90 to inhibit its chaperone function, and significantly induces tumor cell death via an apoptotic mechanism[3].
References

[1]. Tang HB, et al. Viperin inhibits rabies virus replication via reduced cholesterol and sphingomyelin and is regulated upstream by TLR4. Sci Rep. 2016 Jul 26;6:30529

[2]. Chen WW, et al. RIP1 mediates the protection of Geldanamycin on neuronal injury induced by oxygen-glucosedeprivation combined with zVAD in primary cortical neurons. J Neurochem. 2012 Jan;120(1):70-7.

[3]. Lin Z, et al. 17-ABAG, a novel Geldanamycin derivative, inhibits LNCaP-cell proliferation through heat shock protein 90 inhibition. Int J Mol Med. 2015 Aug;36(2):424-32.

[4]. Roe SM, et al. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. J Med Chem. 1999 Jan 28;42(2):260-6.
Density 1.2±0.1 g/cm3
Boiling Point 783.9±60.0 °C at 760 mmHg
Melting Point 255 °C
Molecular Formula C29H40N2O9
Molecular Weight 560.636
Flash Point 427.9±32.9 °C
Exact Mass 560.273376
PSA 163.48000
LogP 2.00
Vapour Pressure 0.0±6.2 mmHg at 25°C
Index of Refraction 1.559
Storage condition −20°C
Water Solubility DMSO: soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LX8920000
CHEMICAL NAME :
Geldanamycin
CAS REGISTRY NUMBER :
30562-34-6
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C29-H40-N2-O9
MOLECULAR WEIGHT :
560.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>4200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Lymphocyte
DOSE/DURATION :
1 mg/L
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 35,886,1982
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes T: Toxic;
Risk Phrases R36/37/38
Safety Phrases 26-27-36/37/39
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS LX8920000
HS Code 2933990090
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
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