Nemadectin | CAS# 102130-84-7 | macrocyclic lactone antibiotic

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

MedKoo CAT#: 413014

CAS#: 102130-84-7

Description: Nemadectin is a macrocyclic lactone antibiotic that demonstrates endectocidal and nematocidal activity. Differing only by the unsaturated side-chain extending from the 6,6-spiroketal core, this antibiotic is structurally similar to milbemycins and avermectins. Nemadectin has been used as starting material for the production of the veterinary anthelmintic, moxidectin, and its derivatives have been explored for their potential antiparasitic use.

Chemical Structure

Nemadectin

CAS# 102130-84-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 413014
Name: Nemadectin
CAS#: 102130-84-7
Chemical Formula: C36H52O8
Exact Mass: 612.37
Molecular Weight: 612.804
Elemental Analysis: C, 70.56; H, 8.55; O, 20.89

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Nemadectin; CL287,088; CL-287,088; CL 287,088

IUPAC/Chemical Name: Milbemycin B, 5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-hydroxy-, (6R,23S,25S(E))-

InChi Key: YNFMRVVYUVPIAN-AQUURSMBSA-N

InChi Code: InChI=1S/C36H52O8/c1-20(2)13-24(6)32-25(7)30(37)18-35(44-32)17-28-16-27(43-35)12-11-22(4)14-21(3)9-8-10-26-19-41-33-31(38)23(5)15-29(34(39)42-28)36(26,33)40/h8-11,13,15,20-21,25,27-33,37-38,40H,12,14,16-19H2,1-7H3/b9-8+,22-11+,24-13+,26-10+/t21-,25-,27+,28-,29-,30-,31+,32+,33+,35-,36+/m0/s1

SMILES Code: CC(/C=C([C@H]1O[C@]2(C[C@@H]([C@@H]1C)O)C[C@@H]3C[C@H](O2)C/C=C(C[C@H](/C=C/C=C4CO[C@@H]5[C@@H](C(C)=C[C@H]([C@]\45O)C(O3)=O)O)C)\C)\C)C

Appearance: Solid powder

Purity: >95% (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: >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:

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Biological target:	Nemadectin (CL-287088), an orally active broad-spectrum endectocide, is highly efficacious against natural infections of all the major canine gastrointestinal helminthes.
In vitro activity:	TBD
In vivo activity:	TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 612.80 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:	TBD
In vitro protocol:	TBD
In vivo protocol:	TBD

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1: Li C, He H, Wang J, Liu H, Wang H, Zhu Y, Wang X, Zhang Y, Xiang W. Characterization of a LAL-type regulator NemR in nemadectin biosynthesis and its application for increasing nemadectin production in Streptomyces cyaneogriseus. Sci China Life Sci. 2019 Mar;62(3):394-405. doi: 10.1007/s11427-018-9442-9. Epub 2019 Jan 15. PMID: 30689104.

2: Song X, Zhang Y, Xue J, Li C, Wang Z, Wang Y. Enhancing nemadectin production by Streptomyces cyaneogriseus ssp. noncyanogenus through quantitative evaluation and optimization of dissolved oxygen and shear force. Bioresour Technol. 2018 May;255:180-188. doi: 10.1016/j.biortech.2017.09.033. Epub 2017 Sep 7. PMID: 29414165.

3: Yang LY, Wang JD, Zhang J, Xue CY, Zhang H, Wang XJ, Xiang WS. New nemadectin congeners with acaricidal and nematocidal activity from Streptomyces microflavus neau3 Y-3. Bioorg Med Chem Lett. 2013 Oct 15;23(20):5710-3. doi: 10.1016/j.bmcl.2013.08.002. Epub 2013 Aug 11. PMID: 23992860.

4: Xiang WS, Wang JD, Wang M, Wang XJ. New nemadectin congener from Streptomyces microflavus neau3: fermentation, isolation, structure elucidation and biological activities. J Antibiot (Tokyo). 2010 Apr;63(4):171-5. doi: 10.1038/ja.2010.12. Epub 2010 Feb 26. PMID: 20186170.

5: Liu H, Zhang Y, Li S, Wang J, Wang X, Xiang W. Elucidation of the Activation Pathways of ScyA1/ScyR1, an Aco/ArpA-Like System That Regulates the Expression of Nemadectin and Other Secondary Metabolic Biosynthetic Genes. Front Bioeng Biotechnol. 2020 Nov 3;8:589730. doi: 10.3389/fbioe.2020.589730. PMID: 33224938; PMCID: PMC7670052.

6: Wang H, Li C, Zhang B, He H, Jin P, Wang J, Zhang J, Wang X, Xiang W. Complete genome sequence of Streptomyces cyaneogriseus ssp. noncyanogenus, the thermotolerant producer of commercial antibiotics nemadectin. J Biotechnol. 2015 Jun 20;204:1-2. doi: 10.1016/j.jbiotec.2015.03.012. Epub 2015 Apr 1. PMID: 25842156.

7: Gao A, Wang X, Xiang W, Liang H, Gao J, Yan Y. Reversal of P-glycoprotein- mediated multidrug resistance in vitro by doramectin and nemadectin. J Pharm Pharmacol. 2010 Mar;62(3):393-9. doi: 10.1211/jpp.62.03.0016. PMID: 20487225.

8: Doscher ME, Wood IB, Pankavich JA, Ricks CA. Efficacy of nemadectin, a new broad-spectrum endectocide, against natural infections of canine gastrointestinal helminths. Vet Parasitol. 1989 Dec;34(3):255-9. doi: 10.1016/0304-4017(89)90055-1. PMID: 2617829.

9: Jin P, Li S, Zhang Y, Chu L, He H, Dong Z, Xiang W. Mining and fine-tuning sugar uptake system for titer improvement of milbemycins in Streptomyces bingchenggensis. Synth Syst Biotechnol. 2020 Jul 14;5(3):214-221. doi: 10.1016/j.synbio.2020.07.001. PMID: 32695892; PMCID: PMC7360889.

10: Garcia-Bustos JF, Sleebs BE, Gasser RB. An appraisal of natural products active against parasitic nematodes of animals. Parasit Vectors. 2019 Jun 17;12(1):306. doi: 10.1186/s13071-019-3537-1. PMID: 31208455; PMCID: PMC6580475.

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