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Pharmakon1600-01500605

HCID 3037037
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Basic information

CAS
128-13-2
Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@@H]3O
InChIKey
RUDATBOHQWOJDD-ZLEVCPGMSA-N
Molecular formula
C24H40O4
Average molar mass
392.6 g/mol
Monoisotopic mass
392.29265975

Names & identifiers

Preferred name
Pharmakon1600-01500605
IUPAC
(4R)-4-[(3R,5S,7S,10S,13R,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
English name
Ursodeoxycholic acid
Molecular formula
C24H40O4
Molecular weight
392.57

Names & synonyms

SR-05000001965Spectrum_000636Spectrum2_000947Spectrum3_000574Spectrum4_000373Spectrum5_001551BSPBio_001988KBioGR_000865KBioSS_001116DivK1c_000416SCHEMBL288251SPECTRUM1500605
Show more names
UDCAURSODIOLUrsodeoxycholicURSODESOXYCHOLIC ACIDURSODEOXYCHOLATETauroursodiol3-alpha,7-beta-dihydroxy-5-beta-cholanoicacidUrosodeoxycholic AcidPorcine deoxycholic acidurso
SPBio_000914CHEMBL1788119HMS501E18KBio1_000416KBio2_001116KBio2_003684KBio2_006252KBio3_001488

Database identifiers

CAS
128-13-2
PubChem CID
3037037
ChEMBL
CHEMBL1788119

Properties

Computed structural properties

XLogP
4.9
Topological polar surface area
77.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
28
Formal charge
0
Complexity
605

Physicochemical properties

Melting point
203 · 203-204 °C (lit.)
alpha
60 · 60 º (c=2, EtOH)
Boiling point
437.26 °C · 437.26°C (rough estimate)
Density
0.9985 · 0.9985 (rough estimate)
refractive index
60.5 ° · 60.5 ° (C=2, EtOH)
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
50 mg/mL, · ethanol: 50 mg/mL, clear
pka
5.04 · pKa 5.04±0.04(H2O t = 25.0±0.1 I = 0.00)(Approximate)
form
Solid. Powder.
color
White - almost white.
Water Solubility
practically insoluble
Merck
14 · 14,9889
BRN
3219888 · 3219888
Cosmetics Ingredients Functions
SKIN CONDITIONING - MISCELLANEOUSSKIN PROTECTING
InChIKey

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
rtecs
FZ2000000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29181990
Toxicity
LD50 in mice (g/kg): 0.1 i.v. (Ardenne, Reitnauer); in rats, mice (mg/kg): 2000, 6000 s.c.; 1000, 1200 i.p., 310, 260 i.v. (Ward)
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
24/25-36-26
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2
Precautionary statements
P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313

Chemistry & industry

Applications · 3 items

UsesUrsodeoxycholic acid is a naturally occurring bile salt in humans. It is rapidly absorbed in the small intestine and excreted with the bile. Ursodeoxycholic acid is the drug of choise for the treatment of primary biliary cirrhosis and primary sclerosis cholanyitis. The daily dose amounts to 10-15 mg/kg. It has no side effects even after a treatment period of up to 20 years.Dissolution of gallstones. Mainly used for the treatment of inoperable cholesterol gallstones, it will have a cure rate especially in the case when gallbladder is basically normal, stones have a 15mm or lower diameters, X-ray penetrable, non-calcified and high-floating cholesterol stones.Ursodeoxycholic acid can also improve the efficacy of α-interferon on treatment of chronic hepatitis C. It can also used to treat diarrhea, rare constipation, allergic reactions, itching, headache, dizziness, stomach pain, pancreatitis and bradycardia Patients of completely biliary obstruction or severe liver dysfunction and pregnant women should avoid using.

UsesUrsodeoxycholic acid (UDCS) is a cell protectant used extensively to mitigate hepatic and biliary diseases. Ursodeoxycholic acid may be used to study its specific activities that range from reduction of cholesterol absorpition, cholesterol gallstone dissolution to suppression of immune response. It is also used as an anticholelithogenic. Epimer with Chenodiol with respect to the hydroxyl group at C7.

General DescriptionUrsodeoxycholic acid (UDCA) is a secondary bile acid that helps regulate cholesterol. Mass spectrometry-based analysis of UDCA is routinely performed in clinical diagnostic testing applications such as neonatal testing of inborn errors of bile acid synthesis, differentiating among types of familial intrahepatic cholestasis, and therapeutic monitoring of patient responses to UDCA therapy. This Certified Spiking Solution is suitable as a starting material in preparation of linearity standards, calibrators, and controls for use in LC-MS/MS and GC/MS bile acid testing methods.

Upstream & downstream products

Upstream raw materials

Diethylene glycol2,3-ButanedioneChenodeoxycholic acid

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
RUDATBOHQWOJDD-UZVSRGJWSA-N
SMILES
C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
LogP
3 · 3-3.38 at 20℃
CAS DataBase Reference
128 · 128-13-2(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
ursodiol
FDA UNII
724 L30Y2QR · 724L30Y2QR
NCI Drug Dictionary
Actigall
ATC code
5 AA02 · A05AA02
UNSPSC Code
41116107 · 41116107
NACRES
25 · NA.25
Protein binding
96 · 96-98%
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
24 · 24/25-36-26
RIDADR
1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany
2 · 2
RTECS
2000000 · FZ2000000
F
10 · 10
HS Code
29181990 · 29181990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2
Toxicity
50 in · LD50 in mice (g/kg): 0.1 i.v. (Ardenne, Reitnauer); in rats, mice (mg/kg): 2000, 6000 s.c.; 1000, 1200 i.p., 310, 260 i.v. (Ward)
REACH Registrations
Active
Cholic acid methyl ester
Potassium chromate
Methanol
Acetylcholic acid
5β-Cholanic acid
Acetic acid
Hydrochloric acid
Chromium(VI) oxide
Sodium

Downstream products

24-norursodeoxycholic acidEthyl UrsodeoxycholateTauroursodeoxycholic acid sodium salt
Additional notes · 1 item

DefinitionChEBI: Ursodeoxycholic acid is a bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of an ursodeoxycholate.