PENITREM A

Modify Date: 2024-01-06 19:15:09

PENITREM A Structure
PENITREM A structure
Common Name PENITREM A
CAS Number 12627-35-9 Molecular Weight 634.201
Density 1.4±0.1 g/cm3 Boiling Point N/A
Molecular Formula C37H44ClNO6 Melting Point N/A
MSDS Chinese USA Flash Point N/A
Symbol GHS06
GHS06
Signal Word Danger

 Use of PENITREM A


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].

 Names

Name penitrem A
Synonym More Synonyms

 PENITREM A 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
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
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

~%

PENITREM A Structure

PENITREM A

CAS#:12627-35-9

Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 1539 - 1540

 Precursor & DownStream

Precursor  1

DownStream  0

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 Synonyms

(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
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