MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 326675 | Name: Limaprost
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Limaprost, also known as ONO 1206 and OP1206, is an analog of PGE1 with structural modifications intended to give it a prolonged half-life and greater potency. Limaprost is orally active. Limaprost reduces motor disturbances by increasing the production of insulin-like growth factor I in rats subjected to spinal cord injury.

Chemical Structure

Limaprost
Limaprost
CAS#74397-12-9 (free)

Theoretical Analysis

MedKoo Cat#: 326675

Name: Limaprost

CAS#: 74397-12-9 (free)

Chemical Formula: C22H36O5

Exact Mass: 380.2563

Molecular Weight: 380.53

Elemental Analysis: C, 69.44; H, 9.54; O, 21.02

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
74397-12-9 (free) 88852-12-4 (alfadex)
Synonym
ONO 1206; ONO 1206; ONO 1206; OP 1206; Limaprost; 17α,20-dimethyl-Δ2-PGE1; 17α,20-dimethyl-Δ2-Prostaglandin E1.
IUPAC/Chemical Name
(2E,11-alpha,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxoprosta-2,13-dien-1-oic acid
InChi Key
OJZYRQPMEIEQFC-UAWLTFRCSA-N
InChi Code
InChI=1S/C22H36O5/c1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/b11-8+,13-12+/t16-,17+,18+,19+,21+/m0/s1
SMILES Code
O=C(O)/C=C/CCCC[C@H]1C(C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C[C@@H](C)CCCC)=O
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Limaprost (OP1206) is a PGE1 analogue and a potent and orally active vasodilator.
In vitro activity:
PGE2, PGE1, and limaprost inhibited the IL-1-mediated induction of NGF in a concentration-dependent manner, with IC50 values of 9.9, 10.6, and 70.9 nM, respectively. PGE1 and limaprost exhibited a novel pharmacological action that suppresses NGF expression in human IVD cells, and other prostanoids differentially regulated NGF expression. Reference: Spine (Phila Pa 1976). 2016 Jun;41(12):E710-E716. https://pubmed.ncbi.nlm.nih.gov/26656048/
In vivo activity:
OP 1206 given orally at more than 100 micrograms/kg relieved vasopressin-induced ST depression of rat electrocardiogram (ECG), an animal model of angina pectoris, concomitant with slight hypotension. Intra-coronary injection of OP 1206 (1-100 ng/kg) in dogs resulted in a remarkable increase of coronary blood flow without any influence on heart rate, blood pressure, myocardial oxygen consumption and redox potential. Reference: Arch Int Pharmacodyn Ther. 1980 Sep;247(1):89-102. https://pubmed.ncbi.nlm.nih.gov/7447563/
Solvent mg/mL mM comments
Solubility
DMSO 40.0 105.12
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 380.53 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Murata K, Sawaji Y, Alimasi W, Suzuki H, Endo K, Tanaka H, Yorifuji M, Kosaka T, Shishido T, Yamamoto K. PGE1 Attenuates IL-1β-induced NGF Expression in Human Intervertebral Disc Cells. Spine (Phila Pa 1976). 2016 Jun;41(12):E710-E716. doi: 10.1097/BRS.0000000000001379. PMID: 26656048. 2. Ney P, Hecker G, Schröder H, Schrör K. Potent inhibition of leukotriene (LT) B4 release from human polymorphonuclear leukocytes (PMN) by the PGE1-analogue OP-1206. Biomed Biochim Acta. 1988;47(10-11):S186-9. PMID: 2470354. 3. Umemura T, Harada N, Kitamura T, Ishikura H, Okajima K. Limaprost reduces motor disturbances by increasing the production of insulin-like growth factor I in rats subjected to spinal cord injury. Transl Res. 2010 Nov;156(5):292-301. doi: 10.1016/j.trsl.2010.08.002. Epub 2010 Sep 8. Erratum in: Transl Res. 2011 Oct;158(4):262. PMID: 20970752. 4. Tsuboi T, Hatano N, Nakatsuji K, Fujitani B, Yoshida K, Shimizu M, Kawasaki A, Sakata M, Tsuboshima M. Pharmacological evaluation of OP 1206, a prostaglandin E1 derivative, as an antianginal agent. Arch Int Pharmacodyn Ther. 1980 Sep;247(1):89-102. PMID: 7447563.
In vitro protocol:
1. Murata K, Sawaji Y, Alimasi W, Suzuki H, Endo K, Tanaka H, Yorifuji M, Kosaka T, Shishido T, Yamamoto K. PGE1 Attenuates IL-1β-induced NGF Expression in Human Intervertebral Disc Cells. Spine (Phila Pa 1976). 2016 Jun;41(12):E710-E716. doi: 10.1097/BRS.0000000000001379. PMID: 26656048. 2. Ney P, Hecker G, Schröder H, Schrör K. Potent inhibition of leukotriene (LT) B4 release from human polymorphonuclear leukocytes (PMN) by the PGE1-analogue OP-1206. Biomed Biochim Acta. 1988;47(10-11):S186-9. PMID: 2470354.
In vivo protocol:
1. Umemura T, Harada N, Kitamura T, Ishikura H, Okajima K. Limaprost reduces motor disturbances by increasing the production of insulin-like growth factor I in rats subjected to spinal cord injury. Transl Res. 2010 Nov;156(5):292-301. doi: 10.1016/j.trsl.2010.08.002. Epub 2010 Sep 8. Erratum in: Transl Res. 2011 Oct;158(4):262. PMID: 20970752. 2. Tsuboi T, Hatano N, Nakatsuji K, Fujitani B, Yoshida K, Shimizu M, Kawasaki A, Sakata M, Tsuboshima M. Pharmacological evaluation of OP 1206, a prostaglandin E1 derivative, as an antianginal agent. Arch Int Pharmacodyn Ther. 1980 Sep;247(1):89-102. PMID: 7447563.
1: Inoue A, Sawada Y, Ohmori S, Omoto D, Haruyama S, Yoshioka M, Nishio D, Nakamura M. Lichenoid Drug Eruption Caused by Limaprost Alfadex. Acta Derm Venereol. 2016 Apr 12. doi: 10.2340/00015555-2435. [Epub ahead of print] PubMed PMID: 27068583. 2: Kim HJ, Kim JH, Park YS, Suk KS, Lee JH, Park MS, Moon SH. Comparative study of the efficacy of limaprost and pregabalin as single agents and in combination for the treatment of lumbar spinal stenosis: a prospective, double-blind, randomized controlled non-inferiority trial. Spine J. 2016 Mar 29. pii: S1529-9430(16)00439-3. doi: 10.1016/j.spinee.2016.02.049. [Epub ahead of print] PubMed PMID: 27045252. 3: Inoue Y, Sekiya N, Yamamoto M, Iohara D, Hirayama F, Uekama K. Formation of the ternary inclusion complex of limaprost with α- and β-cyclodextrins in aqueous solution. Chem Pharm Bull (Tokyo). 2015;63(5):318-25. doi: 10.1248/cpb.c14-00733. PubMed PMID: 25948325. 4: Chen H, Zhang Q, Li X, Zhang H, Sun Y, Yin L, Liu C, Cao Y, Gu J, Ding Y. Single- and multiple-dose pharmacokinetics and tolerability of limaprost in healthy Chinese subjects. Clin Drug Investig. 2015 Mar;35(3):151-7. doi: 10.1007/s40261-014-0265-3. PubMed PMID: 25586152. 5: Kanchiku T, Imajo Y, Suzuki H, Yoshida Y, Taguchi T, Tominaga T, Toyoda K. Comparisons on efficacy of elcatonin and limaprost alfadex in patients with lumbar spinal stenosis and concurrent osteoporosis: a preliminary study using a crossover design. Asian Spine J. 2014 Aug;8(4):469-75. doi: 10.4184/asj.2014.8.4.469. Epub 2014 Aug 19. PubMed PMID: 25187864; PubMed Central PMCID: PMC4149990. 6: Inoue Y, Sekiya N, Katayama K, Narutaki S, Yamamoto M, Iohara D, Hirayama F, Uekama K. Stabilizing effect of β-cyclodextrin on Limaprost, a PGE₁ derivative, in Limaprost alfadex tablets (Opalmon) in highly humid conditions. Chem Pharm Bull (Tokyo). 2014;62(8):786-92. Epub 2014 May 23. PubMed PMID: 24859193. 7: Uesawa M, Muroi K, Ozawa K. Plasmapheresis-refractory transplantation-associated thrombotic microangiopathy successfully treated with pravastatin and limaprost alfadex. Ther Apher Dial. 2013 Aug;17(4):462-3. doi: 10.1111/1744-9987.12015. Epub 2013 Feb 17. PubMed PMID: 23931890. 8: Onda A, Kikuchi S, Yabuki S, Otani K, Nikaido T, Watanabe K, Konno S. Limaprost alfadex and nonsteroidal anti-inflammatory drugs for sciatica due to lumbar spinal stenosis. Eur Spine J. 2013 Apr;22(4):794-801. doi: 10.1007/s00586-012-2551-1. Epub 2012 Oct 23. PubMed PMID: 23090093; PubMed Central PMCID: PMC3631040. 9: Kurokawa R, Nagayama E, Murata H, Kim P. Limaprost alfadex, a prostaglandin E1 derivative, prevents deterioration of forced exercise capability in rats with chronic compression of the spinal cord. Spine (Phila Pa 1976). 2011 May 15;36(11):865-9. doi: 10.1097/BRS.0b013e3181e878a1. PubMed PMID: 21192291. 10: Umemura T, Harada N, Kitamura T, Ishikura H, Okajima K. Limaprost reduces motor disturbances by increasing the production of insulin-like growth factor I in rats subjected to spinal cord injury. Transl Res. 2010 Nov;156(5):292-301. doi: 10.1016/j.trsl.2010.08.002. Epub 2010 Sep 8. Erratum in: Transl Res. 2011 Oct;158(4):262. PubMed PMID: 20970752. 11: Park YS, Park JH, Kim SH, Lee MH, Lee YS, Yang SC, Kang JS. Pharmacokinetic characteristics of a vasodilatory and antiplatelet agent, limaprost alfadex, in the healthy Korean volunteers. Clin Appl Thromb Hemost. 2010 Jun;16(3):326-33. doi: 10.1177/1076029609334125. Epub 2009 Oct 13. PubMed PMID: 19825922. 12: Sugawara T, Hirano Y, Higashiyama N, Mizoi K. Limaprost alfadex improves myelopathy symptoms in patients with cervical spinal canal stenosis. Spine (Phila Pa 1976). 2009 Mar 15;34(6):551-5. doi: 10.1097/BRS.0b013e31819a84ec. PubMed PMID: 19282734. 13: Gauchan P, Andoh T, Kato A, Sasaki A, Kuraishi Y. Effects of the prostaglandin E1 analog limaprost on mechanical allodynia caused by chemotherapeutic agents in mice. J Pharmacol Sci. 2009 Mar;109(3):469-72. Epub 2009 Mar 11. PubMed PMID: 19276613. 14: Nakade S, Komaba J, Ohno T, Kitagawa J, Furukawa K, Miyata Y. Bioequivalence study of two limaprost alfadex 5 microg tablets in healthy subjects: moisture-resistant tablet (dextran formulation) versus standard tablet (lactose formulation). Int J Clin Pharmacol Ther. 2008 Jan;46(1):42-7. PubMed PMID: 18218297. 15: Sugiyama N, Sasayama D, Amano N. Massive epistaxis and subconjunctival hemorrhage due to combination of paroxetine and limaprost alfadex: a case report. Prim Care Companion J Clin Psychiatry. 2007;9(3):240-1. PubMed PMID: 17632667; PubMed Central PMCID: PMC1911174. 16: Komaba J, Masuda Y, Hashimoto Y, Nago S, Takamoto M, Shibakawa K, Nakade S, Miyata Y. Ultra sensitive determination of limaprost, a prostaglandin E1 analogue, in human plasma using on-line two-dimensional reversed-phase liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jun 1;852(1-2):590-7. Epub 2007 Feb 24. PubMed PMID: 17350904. 17: Moribe K, Sekiya N, Fujito T, Yamamoto M, Higashi K, Yokohama C, Tozuka Y, Yamamoto K. Stabilization mechanism of limaprost in solid dosage form. Int J Pharm. 2007 Jun 29;338(1-2):1-6. Epub 2007 Feb 12. PubMed PMID: 17350191. 18: Swainston Harrison T, Plosker GL. Limaprost. Drugs. 2007;67(1):109-18; discussion 119-20. Review. PubMed PMID: 17209669. 19: Tsukamoto H, Nagasawa K. Successful treatment of Raynaud's phenomenon with limaprost, an oral prostaglandin E1 analogue. Br J Rheumatol. 1991 Aug;30(4):317. PubMed PMID: 1863837. 20: Murai C, Sasaki T, Osaki H, Hatakeyama A, Shibata S, Yoshinaga K. Oral limaprost for Raynaud's phenomenon. Lancet. 1989 Nov 18;2(8673):1218. PubMed PMID: 2572927.