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PENITREM A

Names

[ CAS No. ]:
12627-35-9

[ Name ]:
PENITREM A

[Synonym ]:
(2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8S,9aR,14bS,14cR,16aS)-12-chloro-14b,14c,17,17-tetramethyl-10-methylidene-2-(prop-1-en-2-yl)-3,3a,6,6a,7,8,9,9a,10,11,14,14b,14c,15,16,16a-hexadecahydro-2H,4bH-7,8-(epoxymethano)cyclobuta[5,6]benzo[1,2-e]oxireno[4',4a']chromeno[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H)-triol
(2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8S,9aR,14bS,14cR,16aS)-12-Chloro-2-isopropenyl-14b,14c,17,17-tetramethyl-10-methylene-3,3a,6,6a,7,8,9,9a,10,11,14,14b,14c,15,16,16a-hexadecahydro-2H,4bH-7,8-(epoxymethano)cyclobuta[5,6]benzo[1,2-e]oxireno[4',4a']chromeno[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H)-triol
MFCD00083465
PENITREM A
4-Methylhistamine dihydrochloride
2H,6H-Benzo[fg]cyclobut[kl]indeno[1,2-d][3]benzoxocin-14,15-imine-3,4b,11c(5H,6aH)-triol, 12-chloro-3,3a,6b,8,8a,9,9a,10,11,15a,15b,16,17,17a-tetradecahydro-8,8,15a,15b-tetramethyl-10-methylene-2-(1-methylethenyl)-, (2R,3S,3aR,4aS,4bS,6aR,6bS,8aS,9aR,11cR,15aS,15bR,17aS)-
Tremortin A
(2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8S,9aR,14bS,14cR,16aS)-12-Chloro-14b,14c,17,17-tetramethyl-10-methylene-2-(prop-1-en-2-yl)-3,3a,6,6a,7,8,9,9a,10,11,14,14b,14c,15,16,16a-hexadecahydro-2H,4bH-7,8-(epoxymethano)cyclobuta[5,6]benzo[1,2-e]oxireno[4',4a']chromeno[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H)-triol

Biological Activity

[Description]:

Penitrem A is an indole diterpene neurotoxic alkaloid produced by Penicillium, acts as a selective BK channel antagonist with antiproliferative and anti-invasive activities against multiple malignancies. Penitrem A increases the spontaneous release of endogenous glutamate, gamma-aminobutyric acid (GABA) and aspartate from cerebrocortical synaptosomes, and induces tremorgenic syndromes in animals[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Others >> Others
Research Areas >> Neurological Disease

[Target]

BK channel[1]


[References]

[1]. Goda AA, et al. The Maxi-K (BK) Channel Antagonist Penitrem A as a Novel Breast Cancer-Targeted Therapeutic. Mar Drugs. 2018 May 11;16(5).

[2]. Norris PJ, et al. Actions of tremorgenic fungal toxins on neurotransmitter release. J Neurochem. 1980 Jan;34(1):33-42.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Molecular Formula ]:
C37H44ClNO6

[ Molecular Weight ]:
634.201

[ Exact Mass ]:
633.285706

[ PSA ]:
107.47000

[ LogP ]:
6.46

[ Index of Refraction ]:
1.698

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RY7535000
CHEMICAL NAME :
Penitrem A
CAS REGISTRY NUMBER :
12627-35-9
LAST UPDATED :
199304
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C37-H44-Cl-N-O6
MOLECULAR WEIGHT :
634.27

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
41KEAL "Toxicology, Biochemistry and Pathology of Mycotoxins," Uraguchi, K. and M. Yamazaki, eds., New York, John Wiley & Sons, Inc., 1978 Volume(issue)/page/year: -,108,1978
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 17,45,1980
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
500 ug/kg
TOXIC EFFECTS :
Behavioral - tetany Liver - fatty liver degeneration Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 35,311,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
VHTODE Veterinary and Human Toxicology. (American College of Veterinary and Comparative Toxicology, Publication Office, Comparative Toxicology, Manhattan, KS 66506) V.19- 1977- Volume(issue)/page/year: 32(Suppl),63,1990 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
3 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 16,92,1978

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H310-H330

[ Precautionary Statements ]:
P260-P264-P280-P284-P302 + P350-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
R26/27/28

[ Safety Phrases ]:
S45;S36/S37/S39

[ RIDADR ]:
UN 2811 6

[ RTECS ]:
RY7535000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Synthetic Route

Precursor & DownStream

Precursor

DownStream

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