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Home > Encyclopedia > Deoxycholic acid

Deoxycholic acid

pharmaceutical raw materials
Deoxycholic acid structure

Deoxycholic acid 

structure
  • CAS No:

    83-44-3

  • Formula:

    C24H40O4

  • Chemical Name:

    Deoxycholic acid

  • Synonyms:

    Cholan-24-oic acid,3,12-dihydroxy-,(3α,5β,12α)-;5β-Cholan-24-oic acid,3α,12α-dihydroxy-;(3α,5β,12α)-3,12-Dihydroxycholan-24-oic acid;Cholic acid,deoxy-;Cholorebic;Degalol;Deoxycholatic acid;Deoxycholic acid;Desoxycholic acid;3α,12α-Dihydroxycholanic acid;3α,12α-Dihydroxy-5β-cholanoic acid;Droxolan;17β-[1-Methyl-3-carboxypropyl]-etiocholane-3α,12α-diol;3α,12α-Dihydroxy-5β-cholanic acid;Cholerebic;Pyrochol;Septochol;3α,12α-Dihydroxy-5β-cholan-24-oic acid;5β-Deoxycholic acid;5β-Cholanic acid-3α,12α-diol;7-Deoxycholic acid;NSC 8797;ATX 101;Kybella;728917-93-9

  • Categories:

    Cosmetic Ingredient  >  Skin Conditioning

Description

Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity.


Solid


Deoxycholic acid is a bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively. It has a role as a human blood serum metabolite. It is a bile acid, a dihydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of a deoxycholate.|Deoxycholic acid is a a bile acid which emulsifies and solubilizes dietary fats in the intestine, and when injected subcutaneously, it disrupts cell membranes in adipocytes and destroys fat cells in that tissue. In April 2015, deoxycholic acid was approved by the FDA for the treatment submental fat to improve aesthetic appearance and reduce facial fullness or convexity. It is marketed under the brand name Kybella by Kythera Biopharma and is the first pharmacological agent available for submental fat reduction, allowing for a safer and less invasive alternative than surgical procedures.|Deoxycholic acid is a Cytolytic Agent. The physiologic effect of deoxycholic acid is by means of Decreased Cell Membrane Integrity.|A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.

Deoxycholic acid Basic Attributes

392.57

392.57

3219882

201-478-5

005990WHZZ

8797

DTXSID0042662

CRYSTALS FROM ALC

D - Dermatologicals

29181990

Characteristics

77.8

4.9

Solid

1.1±0.1 g/cm3

176-178 °C

547.1ºC at 760 mmHg

9℃

1.543

H2O: 0.24 g/L (15 ºC)

Store at RT.

LD50 oral in rat: 1gm/kg

55 º (c=1, EtOH)

pK= 6.58

200.7 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|209.86 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|202.2 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|202.3 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|196.7 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|202.1 Ų [M-H]-

Safety Information

UN1230 - class 3 - PG 2 - Methanol, solution

3

22-36/37/38-37-20/21/22

26-36-37/39-22

FZ2100000

Xn

Stable. Combustible. Incompatible with strong oxidizing agents.

P301 + P312 + P330

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

...COMPETITION FOR EXTRAVASCULAR BINDING SITES BY DEOXYCHOLIC ACID MAY EXPLAIN REDUCED VOL OF DISTRIBUTION OF BROMSULFOPHTHALEIN IN PRESENCE OF BILE ACID.|COMPD INCL DEOXYCHOLATE POTENTIATED ANTISTAPHYLOCOCCI ACTIVITY OF GENTAMYCIN, MONOMYCIN, KANAMYCIN, & NEOMYCIN.|Deoxycholic acid was tested alone and as a promoter of N-nitrosobis(2-hydroxypropyl)amine induced carcinogenesis in the hamster. Three groups of 5 to 6-wk-old male Syrian hamsters (SYR)/NI were used and 10 animals per group were given subcutaneous injections of 0.9% NaCl, once per week for 5 weeks. Group 1 received no further treatment; groups 2 and 3 received 0.1% and 0.5% DCA in their feed for 30 weeks, respectively. Animals were autopsied at week 35. There was no significant difference in body wt. between groups 1 and 2, whereas there was a significant decrease in body weight for group 3 (P<0.005). There were no liver tumors, bile duct proliferation, gallbladder lesions or polyps, pancreatic lesions, or pancreatic duct hyperplasia in these 3 groups. In the promoter study, three groups of 5 to 6-wk-old hamsters (number not stated) were given a subcutaneous injection of 500 mg/kg body wt. N-nitrosobis(2-hydroxypropyl)amine per week for 5 weeks. Group 4 received no further treatment and the N-nitrosobis(2-hydroxypropyl)amine treatment was followed by 0.1% DCA (group 5) , or 0.5% DCA (group 6) in the feed for 30 weeks. There was a significant body weight loss (P<0.005) for groups 5 and 6 compared to group 4. DCA significantly increased the induction of cholangiocarcinomas 10/19 in group 5 (P<0.006); 9/25 in group 6 (P<0.05) compared to group 4 which had 1/15. Pancreatic carcinomas were significantly increased in group 5 (14/19, P<0.03). Therefore, under the conditions of this experiment, DCA was not carcinogenic when given alone but was an effective promoter of N-nitrosobis(2-hydroxypropyl)amine-induced hepatic and pancreatic carcinogenesis in hamsters.

98%

DEOXYCHOLIC /ACID IS/...FORMED IN INTESTINE BY ACTION OF /ENTERIC/ BACTERIA ON SECRETED BILE ACIDS.|OCCURS IN BILE OF MAN, OX, SHEEP, DOG, GOAT & RABBIT.

Drug Information

For improvement in appearance of moderate to severe fullness associated with submental fat in adults.|FDA Label|Treatment of localised fat deposits

Cholagogues and Choleretics; Detergents|The useful effects of exogenous bile acids result from their capacity to decrease the cholesterol content of the bile and promote dissolution of cholesterol gallstones. /Bile acids/|VET USE: TO INCR VOL OF BILE WITHOUT SIGNIFICANTLY ALTERING PROPORTIONS OF ITS CONSTITUENTS. MOST EFFECTIVE BILE ACID IN AIDING ABSORPTION OF FATS & FAT-SOLUABLE VITAMINS.

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)

Deoxycholic acid is rapidly absorbed after subcutaneous administration. After maximum recommended single treatment dose, 100mg, the post-treatment plasma levels returned to endogenous levels within 24 hours. With the proposed treatment guideline, no accumulation is expected.|The exogenous deoxycholic acid joins the endogenous bile acid pool in the enterohepatic circulation and is excreted unchanged in feces along with endogenous deoxycholic acid.|LIVER NORMALLY SECRETES APPROX 24 G OF BILE SALTS IN 700 TO 1000 ML OF BILE IN 24 HR. MOST OF BILE SALTS ARE REABSORBED IN LOWER SMALL INTESTINE & AGAIN BECOME AVAILABLE FOR SECRETION. ... POOL OF BILE SALTS IS APPROX 2 TO 5 G. /BILE SALTS/

Deoxycholic acid is not metabolized to any significant extent under normal conditions.

As a bile acid, deoxycholic acid emulsifies fat in the gut. Synthetically derived deoxycholic acid, when injected, stimulates a targeted breakdown of adipose cells by disrupting the cell membrane and causing adipocytolysis. This results in an inflammatory reaction and clearing of the adipose tissue remnants by macrophages. Deoxycholic acid's actions are reduced by albumin and tissue-associated proteins, therefore its effect is limited to protein-poor subcutaneous fat tissue. Protein-rich tissues like muscle and skin are unaffected by deoxycholic acid, contributing to its safety profile.|IN SOLN CONJUGATED BILE SALTS FORM MICELLES IN WHICH LIPID MATERIALS MAY BE ENTRAINED. ...ALSO PROMOTE DIGESTION OF FATS BY STIMULATING PANCREATIC SECRETION & BY ACTIVATING PANCREATIC LIPASE. ... DEOXYCHOLIC.../ACID/ PROMOTE/S/ NET EXCRETION OF NA, K, & WATER IN COLON...MAY BE...FACTORS REGULATING COLONIC ABSORPTION.|DEOXYCHOLATE ADMIN DECR ABSORPTION OF CHOLESTEROL FROM HUMAN INTESTINAL TRACT. IT APPEARED TO INFLUENCE INTESTINAL FLORA AS ASSESSED INDIRECTLY BY ANALYSIS OF TYPES OF NEUTRAL STEROLS ELIM WITH FECES.

Excess bile acids reaching the colon can reduce net water absorption and cause diarrhea. /Bile acids/|FOLLOWING IV INJECTION OF BILE SALTS...THERE IS MARKED FALL IN BLOOD PRESSURE ACCOMPANIED BY A BRADYCARDIA. ...JAUNDICE... IV, BILE SALTS CAUSE SKELETAL MUSCULAR HYPERACTIVITY, TWITCHING, SPASM, DECR IN THRESHOLD FOR NERVE IMPULSES. ...BILE ACIDS...CAUSE LYSIS OF RED & WHITE BLOOD CELLS. /BILE SALTS & BILE ACIDS/

12beta-Isomer Deoxycholic Acid

Deoxycholic acid Use and Manufacturing

Methods of Manufacturing

ISOLATION: WIELAND, SIEBERT, Z PHYSIOL CHEM 262, 1 (1939). FROM CHOLIC ACID: SIFFERD, US PATENT 2,765,316 (1956 TO ARMOUR). STRUCTURE & SYNTHESIS: LF LIESER, M FIESER, STEROIDS (REINHOLD, NY, 1959). LAB PREPN FROM OX BILE: GATTERMANN-WIELAND, PRAXIS DES ORGANISCHEN CHEMIKERS (DE GRUYTER, BERLIN, 40TH ED, 1961) PAGE 361.|Isolation from bile.

Uses

antiinflammatory, immunomodulator, antineoplastic

GRADES: TECHNICAL; FCC (AS DESOXYCHOLIC ACID)

Cholan-24-oic acid, 3,12-dihydroxy-, (3.alpha.,5.beta.,12.alpha.)-: ACTIVE|COMPLEXES WITH FATTY ACIDS HAVE BEEN STUDIED EXTENSIVELY: SOBOTKA, GOLDBERG, BIOCHEM J 26, 555 (1932); SOBOTKA, CHEM REV 15, 362 (1934). SURFACE ACTIVITY: IDEM, CHEMISTRY OF THE STEROIDS, NY (1938).|BILE ACIDS DO NOT OCCUR IN BILE AS SUCH BUT RATHER AS THE SALT FORM CONJUGATED WITH TAURINE OR GLYCINE. /BILE ACIDS/|AN ADDUCT WITH MENTHOL IS MARKETED UNDER NAME DEGALOL.|FORMS MOLECULAR COORDINATION COMPD (SO CALLED CHOLEIC ACIDS) WITH MANY SUBSTANCES;

Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Lipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]

Food Additives -> EMULSIFIER;

Computed Properties

Molecular Weight:392.6
XLogP3:4.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:392.29265975
Monoisotopic Mass:392.29265975
Topological Polar Surface Area:77.8
Heavy Atom Count:28
Complexity:605
Defined Atom Stereocenter Count:10
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Related Drugs

Registered Holders

  • CURIA SPAIN SAU

    United States United States
    Active
  • Curia Spain S.A.U.

    South Korea South Korea
    Active
  • Yantai Ningyuan Pharmaceutical Co., Ltd.

    China China
    Active

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