Indomethacin
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MedKoo CAT#: 205971

CAS#: 53-86-1

Description: Indomethacin is a synthetic nonsteroidal indole derivative with anti-inflammatory activity and chemopreventive properties. As a nonsteroidal anti-inflammatory drug (NSAID), indomethacin inhibits the enzyme cyclooxygenase, thereby preventing cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines. This agent also may inhibit the expression of multidrug-resistant protein type 1, resulting in increased efficacies of some antineoplastic agents in treating multi-drug resistant tumors. In addition, indomethacin activates phosphatases that inhibit the migration and proliferation of cancer cells and downregulates survivin, which may result in tumor cell apoptosis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)


Chemical Structure

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Indomethacin
CAS# 53-86-1

Theoretical Analysis

MedKoo Cat#: 205971
Name: Indomethacin
CAS#: 53-86-1
Chemical Formula: C19H16ClNO4
Exact Mass: 357.07679
Molecular Weight: 357.79
Elemental Analysis: C, 63.78; H, 4.51; Cl, 9.91; N, 3.91; O, 17.89

Size Price Shipping out time Quantity
1g USD 200 Same day
10g USD 250 Same day
100g USD 550 2 Weeks
500g USD 1450 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-08. Prices are subject to change without notice.

Indomethacin, purity > 98%, is in stock. The same day shipping after order is received.

Synonym: Indomethacin; Indometacin; Indocin.

IUPAC/Chemical Name: 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

InChi Key: CGIGDMFJXJATDK-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)

SMILES Code: O=C(O)CC1=C(C)N(C(C2=CC=C(Cl)C=C2)=O)C3=C1C=C(OC)C=C3

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 357.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Nalamachu S, Wortmann R. Role of indomethacin in acute pain and inflammation management: a review of the literature. Postgrad Med. 2014 Jul;126(4):92-7. doi: 10.3810/pgm.2014.07.2787. Review. PubMed PMID: 25141247.

2: Pacifici GM. Differential renal adverse effects of ibuprofen and indomethacin in preterm infants: a review. Clin Pharmacol. 2014 Jul 31;6:111-6. doi: 10.2147/CPAA.S59376. eCollection 2014. Review. PubMed PMID: 25114597; PubMed Central PMCID: PMC4124049.

3: Sethi S, Sethi N, Wadhwa V, Garud S, Brown A. A meta-analysis on the role of rectal diclofenac and indomethacin in the prevention of post-endoscopic retrograde cholangiopancreatography pancreatitis. Pancreas. 2014 Mar;43(2):190-7. doi: 10.1097/MPA.0000000000000090. Review. PubMed PMID: 24518496.

4: Pacifici GM. Clinical pharmacology of indomethacin in preterm infants: implications in patent ductus arteriosus closure. Paediatr Drugs. 2013 Oct;15(5):363-76. doi: 10.1007/s40272-013-0031-7. Review. PubMed PMID: 23754139.

5: Summ O, Evers S. Mechanism of action of indomethacin in indomethacin-responsive headaches. Curr Pain Headache Rep. 2013 Apr;17(4):327. doi: 10.1007/s11916-013-0327-x. Review. PubMed PMID: 23423598.

6: Chiba H, Masutani S, Toyoshima K, Mori R. Indomethacin for preterm infants with intracranial hemorrhage. Pediatr Int. 2013 Feb;55(1):124-6. doi: 10.1111/ped.12037. Review. PubMed PMID: 23409994.

7: Bonzi M, Fiorelli EM; Gruppo di Autoformazione Metodologica (GrAM). Indomethacin prevents post-ERCP pancreatitis in selected high-risk patients. Intern Emerg Med. 2012 Dec;7(6):557-8. doi: 10.1007/s11739-012-0872-z. Epub 2012 Nov 2. Review. PubMed PMID: 23117274.

8: Szabó IL, Czimmer J, Szolcsányi J, Mózsik G. Molecular pharmacological approaches to effects of capsaicinoids and of classical antisecretory drugs on gastric basal acid secretion and on indomethacin-induced gastric mucosal damage in human healthy subjects (mini review). Curr Pharm Des. 2013;19(1):84-9. Review. PubMed PMID: 22946903.

9: Neumann R, Schulzke SM, Bührer C. Oral ibuprofen versus intravenous ibuprofen or intravenous indomethacin for the treatment of patent ductus arteriosus in preterm infants: a systematic review and meta-analysis. Neonatology. 2012;102(1):9-15. doi: 10.1159/000335332. Epub 2012 Mar 8. Review. PubMed PMID: 22414850.

10: Johnston PG, Gillam-Krakauer M, Fuller MP, Reese J. Evidence-based use of indomethacin and ibuprofen in the neonatal intensive care unit. Clin Perinatol. 2012 Mar;39(1):111-36. doi: 10.1016/j.clp.2011.12.002. Epub 2012 Jan 13. Review. PubMed PMID: 22341541; PubMed Central PMCID: PMC3598606.

11: Anabrees JA, Aifaleh KM. Fluid restriction and prophylactic indomethacin in extremely low birth weight infants. J Clin Neonatol. 2012 Jan;1(1):1-5. doi: 10.4103/2249-4847.92228. Review. PubMed PMID: 24027673; PubMed Central PMCID: PMC3761987.

12: Anabrees J, Alfaleh K. Fluid restriction and prophylactic indomethacin versus prophylactic indomethacin alone for prevention of morbidity and mortality in extremely low birth weight infants. Cochrane Database Syst Rev. 2011 Jul 6;(7):CD007604. doi: 10.1002/14651858.CD007604.pub2. Review. PubMed PMID: 21735414.

13: Longhi A, Errani C, Battaglia M, Alberghini M, Ferrari S, Mercuri M, Molinari M. Aggressive fibromatosis of the neck treated with a combination of chemotherapy and indomethacin. Ear Nose Throat J. 2011 Jun;90(6):E11-5. Review. PubMed PMID: 21674455.

14: Fujino H, Murayama T. [Novel anti-cancer effects of indomethacin: exploring the cyclooxygenase-inhibition-independent effects]. Nihon Yakurigaku Zasshi. 2011 Apr;137(4):177-81. Review. Japanese. PubMed PMID: 21478637.

15: Hoy SM, Scott LJ. Indomethacin/prochlorperazine/caffeine: a review of its use in the acute treatment of migraine and in the treatment of episodic tension-type headache. CNS Drugs. 2011 Apr;25(4):343-58. doi: 10.2165/11206740-000000000-00000. Review. PubMed PMID: 21425885.

16: Jones LJ, Craven PD, Attia J, Thakkinstian A, Wright I. Network meta-analysis of indomethacin versus ibuprofen versus placebo for PDA in preterm infants. Arch Dis Child Fetal Neonatal Ed. 2011 Jan;96(1):F45-52. doi: 10.1136/adc.2009.168682. Epub 2010 Sep 27. Review. PubMed PMID: 20876595.

17: Prakash S, Shah ND, Chavda BV. Cluster headache responsive to indomethacin: Case reports and a critical review of the literature. Cephalalgia. 2010 Aug;30(8):975-82. doi: 10.1177/0333102409357642. Epub 2010 Mar 12. Review. PubMed PMID: 20656709.

18: Fowlie PW, Davis PG, McGuire W. Prophylactic intravenous indomethacin for preventing mortality and morbidity in preterm infants. Cochrane Database Syst Rev. 2010 Jul 7;(7):CD000174. doi: 10.1002/14651858.CD000174.pub2. Review. PubMed PMID: 20614421.

19: Suleyman H, Albayrak A, Bilici M, Cadirci E, Halici Z. Different mechanisms in formation and prevention of indomethacin-induced gastric ulcers. Inflammation. 2010 Aug;33(4):224-34. doi: 10.1007/s10753-009-9176-5. Review. PubMed PMID: 20084447.

20: Prakash S, Shah ND, Bhanvadia RJ. Hemicrania continua unresponsive or partially responsive to indomethacin: does it exist? A diagnostic and therapeutic dilemma. J Headache Pain. 2009 Feb;10(1):59-63. doi: 10.1007/s10194-008-0088-9. Epub 2008 Dec 19. Review. PubMed PMID: 19096758; PubMed Central PMCID: PMC3451756.



Additional Information

Indometacin (INN and BAN) or indomethacin (AAN, USAN and former BAN) is a non-steroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms.  It is marketed under more than twelve different trade names.   
 
Clinical indications for indometacin include:
Hemicrania continua
ankylosing spondylitis
arthritic gout
Bartter syndrome
bursitis
cryoglobulinemia
dysmenorrhea (menstrual cramps)
exertion headache
fever and pain associated with malignant diseases (especially tumor fever associated with liver involvement, lymphogranulomatosis)
hemicrania continua
hypnic headache
juvenile arthritis
migraine
patent ductus arteriosus
nephrogenic diabetes insipidus (prostaglandin inhibits vasopressin's action in the kidney)
osteoarthritis
Paget's disease of bone
paroxysmal hemicrania
pericarditis
primary stabbing headaches
pseudogout
psoriatic arthritis
Reactive arthritis
renal colic (pain due to kidney stones)
retinopathy of prematurity
rheumatoid arthritis
tendinitis
trigeminal autonomic cephalgias
Headaches induced by or otherwise a result of Valsalva maneuver
Indomethacin has also been used clinically to delay premature labor, reduce amniotic fluid in polyhydramnios, and to close patent ductus arteriosus.
Indomethacin is a potent drug with many serious side effects and should not be considered an analgesic for minor aches and pains or fever. The medication is better described as an anti-inflammatory, rather than an analgesic. Indomethacin can also affect warfarin and subsequently raise INR.