Linderane | CAS#13476-25-0 | cytochrome P450 2C9 inhibitor

MedKoo Cat#: 598919 | Name: Linderane

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Description:

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

Linderane is a cytochrome P450 2C9 inhibitor from Lindera aggregata (Sims).

Chemical Structure

Linderane

CAS#13476-25-0

Theoretical Analysis

MedKoo Cat#: 598919

Name: Linderane

CAS#: 13476-25-0

Chemical Formula: C15H16O4

Exact Mass: 260.1049

Molecular Weight: 260.29

Elemental Analysis: C, 69.22; H, 6.20; O, 24.59

Price and Availability

Size	Price	Availability
10mg	USD 300.00	2 Weeks
25mg	USD 600.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

No Data

Synonym

Linderane;

IUPAC/Chemical Name

(10S,10aS,E)-5,9-dimethyl-3,6,10,10a-tetrahydro-2H-10,1a-(epoxymethano)oxireno[2',3':4,5]cyclodeca[1,2-b]furan-12-one

InChi Key

KBMSVODXFLAQNJ-IUKAEILTSA-N

InChi Code

InChI=1S/C15H16O4/c1-8-4-3-5-15-13(19-15)12(18-14(15)16)11-9(2)7-17-10(11)6-8/h4,7,12-13H,3,5-6H2,1-2H3/b8-4+/t12-,13-,15?/m0/s1

SMILES Code

Cc1c([C@H]2[C@H]3C(CC/C=C(C)/C4)(C(O2)=O)O3)c4oc1

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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Linderane, isolated from the root of Lindera aggregata, is an irreversible inhibitor cytochrome P450 2C9 (CYP2C9).

In vitro activity:

LDR (linderane) caused a time- and concentration-dependent inactivation of CYP2C9. In addition, the inactivation of CYP2C9 by LDR was NADPH-dependent and irreversible. More than 50% of CYP2C9 activity was lost after its incubation with LDR at the concentration of 10 μM for 15 min at 30 °C. Reference: Xenobiotica. 2015;45(12):1037-46. https://pubmed.ncbi.nlm.nih.gov/26068520/

In vivo activity:

The chronic glucose-lowering potential of linderane (50 mg kg-1, twice a day) was evaluated in male ob/ob mice. Treatment with linderane significantly decreased random-fed and fast blood glucose levels with a reduction rate of 49.4 and 30.2%, respectively, after 20 days of treatment (Figures 7A,B). Reference: Front Pharmacol. 2018 May 15;9:476. https://pubmed.ncbi.nlm.nih.gov/29867482/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	38.42
	DMF:PBS (pH 7.2) (1:10)	0.1	0.35
	DMSO	52.5	201.70
	Ethanol	0.2	0.77

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 260.29 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.

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. Zhang H, Zhu C, Sun Z, Yan X, Wang H, Xu H, Ma J, Zhang Y. Linderane protects pancreatic β cells from streptozotocin (STZ)-induced oxidative damage. Life Sci. 2019 Sep 15;233:116732. doi: 10.1016/j.lfs.2019.116732. Epub 2019 Aug 5. PMID: 31394125. 2. Wang H, Wang K, Mao X, Zhang Q, Yao T, Peng Y, Zheng J. Mechanism-based inactivation of CYP2C9 by linderane. Xenobiotica. 2015;45(12):1037-46. doi: 10.3109/00498254.2015.1041002. Epub 2015 Jun 11. PMID: 26068520. 3. Xie W, Ye Y, Feng Y, Xu T, Huang S, Shen J, Leng Y. Linderane Suppresses Hepatic Gluconeogenesis by Inhibiting the cAMP/PKA/CREB Pathway Through Indirect Activation of PDE 3 via ERK/STAT3. Front Pharmacol. 2018 May 15;9:476. doi: 10.3389/fphar.2018.00476. PMID: 29867482; PMCID: PMC5962748.

In vitro protocol:

In vivo protocol:

1. Xie W, Ye Y, Feng Y, Xu T, Huang S, Shen J, Leng Y. Linderane Suppresses Hepatic Gluconeogenesis by Inhibiting the cAMP/PKA/CREB Pathway Through Indirect Activation of PDE 3 via ERK/STAT3. Front Pharmacol. 2018 May 15;9:476. doi: 10.3389/fphar.2018.00476. PMID: 29867482; PMCID: PMC5962748.

1: Wang H, Wang K, Mao X, Zhang Q, Yao T, Peng Y, Zheng J. Mechanism-based inactivation of CYP2C9 by linderane. Xenobiotica. 2015;45(12):1037-46. doi: 10.3109/00498254.2015.1041002. Epub 2015 Jun 11. PubMed PMID: 26068520. 2: Yaermaimaiti S, Wang P, Luo J, Li RJ, Kong LY. Sesquiterpenoids from the seeds of Sarcandra glabra and the potential anti-inflammatory effects. Fitoterapia. 2016 Jun;111:7-11. doi: 10.1016/j.fitote.2016.03.020. Epub 2016 Apr 2. PubMed PMID: 27050720. 3: Cai LH, Chou GX, Wang ZT, Li YG, Xu DR, Xu LS. [Determination of linderane in root tuber of Lindera aggregata by HPLC]. Zhongguo Zhong Yao Za Zhi. 2004 Jul;29(7):657-9. Chinese. PubMed PMID: 15503773. 4: Gan LS, Zheng YL, Mo JX, Liu X, Li XH, Zhou CX. Sesquiterpene lactones from the root tubers of Lindera aggregata. J Nat Prod. 2009 Aug;72(8):1497-501. doi: 10.1021/np900354q. PubMed PMID: 19639966. 5: Zheng Y, Luan L, Gan L, Zhou C, Wu Y. [Simultaneous determination of three sesquiterpene lactones in Radix Linderae by HPLC]. Zhongguo Zhong Yao Za Zhi. 2009 Nov;34(21):2777-80. Chinese. PubMed PMID: 20209914. 6: Xie W, Ye Y, Feng Y, Xu T, Huang S, Shen J, Leng Y. Linderane Suppresses Hepatic Gluconeogenesis by Inhibiting the cAMP/PKA/CREB Pathway Through Indirect Activation of PDE 3 via ERK/STAT3. Front Pharmacol. 2018 May 15;9:476. doi: 10.3389/fphar.2018.00476. eCollection 2018. PubMed PMID: 29867482; PubMed Central PMCID: PMC5962748. 7: Wu Y, Zheng Y, Liu X, Han Z, Ren Y, Gan L, Zhou C, Luan L. Separation and quantitative determination of sesquiterpene lactones in Lindera aggregata (wu-yao) by ultra-performance LC-MS/MS. J Sep Sci. 2010 Apr;33(8):1072-8. doi: 10.1002/jssc.200900768. PubMed PMID: 20187034. 8: Cheng XL, Ma SC, Wei F, Wang GL, Xiao XY, Lin RC. A new sesquiterpene isolated from Lindera aggregata (SIMS) KOSTERM. Chem Pharm Bull (Tokyo). 2007 Sep;55(9):1390-2. PubMed PMID: 17827769. 9: Choi JE, Park DM, Chun E, Choi JJ, Seo JH, Kim S, Son J, Do M, Kim SY, Park YC, Jung IC, Jin M. Control of stress-induced depressive disorders by So-ochim-tang-gamibang, a Korean herbal medicine. J Ethnopharmacol. 2017 Jan 20;196:141-150. doi: 10.1016/j.jep.2016.12.025. Epub 2016 Dec 15. PubMed PMID: 27988398. 10: He Y, Cheng P, Wang W, Yan S, Tang Q, Liu D, Xie H. Rapid Investigation and Screening of Bioactive Components in Simo Decoction via LC-Q-TOF-MS and UF-HPLC-MD Methods. Molecules. 2018 Jul 20;23(7). pii: E1792. doi: 10.3390/molecules23071792. PubMed PMID: 30036998.