Prostaglandin D2

Names

[ Name ]:
Prostaglandin D2

[Synonym ]:
PGD2
(5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic acid
Prosta-5,13-dien-1-oic acid, 9,15-dihydroxy-11-oxo-, (5Z,9α,13E,15S)-
Prostaglandin D2
(5Z,9α,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid
MFCD00077857

Biological Activity

[Description]:

Prostaglandin D2 (PGD2) is one of the major PGs actively produced in the brain of various mammals[1]. Prostaglandin D2 is one of the most potent endogenous sleep promoting substances[2]. PGD2 plays a protective role by suppressing inflammation[3].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite

[In Vivo]

Prostaglandin D2 (PGD2; infused into the lateral ventricle; 5-50 pmol/min; for 6 hours between 20:00 and 2:00) induces sleep-wake profiles in A2AR KO mice[2]. Animal Model: Male WT and A2AR KO mice of the inbred C57BL/6 strain (weighing 23-27 g, 11-13 weeks old)[1] Dosage: 5, 10, 20, or 50 pmol/min Administration: Infused into the lateral ventricle; for 6 hours between 20:00 and 2:00 Result: Induced sleep-wake profiles.

[References]

[1]. Suzuki F, et al. Transport of prostaglandin D2 into brain. Brain Res. 1986 Oct 22;385(2):321-8.

[2]. Zhang BJ, et al. Adenosine A2A receptor deficiency attenuates the somnogenic effect of prostaglandin D2 in mice. Acta Pharmacol Sin. 2017 Apr;38(4):469-476.

[3]. Kida T, et al. Prostaglandin D2 Attenuates Bleomycin-Induced Lung Inflammation and Pulmonary Fibrosis. PLoS One. 2016 Dec 19;11(12):e0167729.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
549.6±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₃₂O₅

[ Molecular Weight ]:
352.465

[ Flash Point ]:
300.3±26.6 °C

[ Exact Mass ]:
352.224976

[ PSA ]:
94.83000

[ LogP ]:
2.02

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.561

[ Storage condition ]:
20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UK7930000

CHEMICAL NAME :: Prosta-5,13-dien-1-oic acid, 9,15-dihydroxy-11-oxo-, (5Z,9-alpha,13E,15S)-

CAS REGISTRY NUMBER :: 41598-07-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C20-H32-O5

MOLECULAR WEIGHT :: 352.52

WISWESSER LINE NOTATION :: T5VTJ B1U7 C2U4VQ DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 ug/kg

SEX/DURATION :: female 4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Cells - not otherwise specified

DOSE/DURATION :: 5 mg/L/24H

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 46,1688,1986

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H360

[ Precautionary Statements ]:
P201-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;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: Toxic;

[ Risk Phrases ]:
60-22

[ Safety Phrases ]:
S22;S26;S36;S53

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
UK7930000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...

The human serum metabolome.

PLoS ONE 6(2) , e16957, (2011)

Continuing improvements in analytical technology along with an increased interest in performing comprehensive, quantitative metabolic profiling, is leading to increased interest pressures within the m...

Malva sylvestris L. extract suppresses desferrioxamine-induced PGE₂ and PGD₂ release in differentiated U937 cells: the development and validation of an LC-MS/MS method for prostaglandin quantification.

Biomed. Chromatogr. 28(7) , 986-93, (2014)

Malva sylvestris is a species used worldwide as an alternative to anti-inflammatory therapies; however, its mechanism of action remains unknown. In this paper, the anti-inflammatory effects of M. sylv...