Ivermectin B1b
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| Category | Bioactive by-products |
| Catalog number | BBF-03934 |
| CAS | 70209-81-3 |
| Molecular Weight | 861.06 |
| Molecular Formula | C47H72O14 |
| Purity | >95% by HPLC |
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Description
Ivermectin B1b is a minor component of Ivermectin, a semi-synthetic derivative of Abamectin. Ivermectin is a medication that is effective against many types of parasites.
Specification
| Synonyms | Dihydroavermectin B1b; 22,23-Dihydroavermectin B1b; Avermectin H2B1b |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethyl-6'-propan-2-ylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one |
| Canonical SMILES | CC1CCC2(CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)OC1C(C)C |
| InChI | InChI=1S/C47H72O14/c1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h11-14,18,24-25,27,29-30,32-44,48-49,51H,15-17,19-23H2,1-10H3/b12-11+,26-14+,31-13+/t25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m0/s1 |
| InChI Key | VARHUCVRRNANBD-PVVXTEPVSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | parasites |
| Melting Point | 155°C |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Toxicity
| Carcinogenicity | Not listed by IARC. |
| Mechanism Of Toxicity | Ivermectin binds selectively and with high affinity to glutamate-gated chloride ion channels in invertebrate muscle and nerve cells of the microfilaria. This binding causes an increase in the permeability of the cell membrane to chloride ions and results in hyperpolarization of the cell, leading to paralysis and death of the parasite. Ivermectin also is believed to act as an agonist of the neurotransmitter gamma-aminobutyric acid (GABA), thereby disrupting GABA-mediated central nervous system (CNS) neurosynaptic transmission. Ivermectin may also impair normal intrauterine development of O. volvulus microfilariae and may inhibit their release from the uteri of gravid female worms. It has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. |
| Toxicity | LD50 = 29.5 mg/kg (Mouse, oral); LD50 = 10 mg/kg (Rat, oral). |
Reference Reading
1.Inhibition of P-glycoprotein in the blood-brain barrier alters avermectin neurotoxicity and swimming performance in rainbow trout.
Kennedy CJ1, Tierney KB2, Mittelstadt M3. Aquat Toxicol. 2014 Jan;146:176-85. doi: 10.1016/j.aquatox.2013.10.035. Epub 2013 Nov 7.
The importance of the blood brain barrier (BBB) and the contribution to its function by the efflux transporter P-glycoprotein (P-gp) in teleosts were examined using the P-gp substrates and central nervous system neurotoxins ivermectin (22,23-dihydroavermectin B1a+22,23-dihydroavermectin B1b) [IVM]) and emamectin benzoate (4″-deoxy-49″epimethylaminoavermectin B1 benzoate [EB]). Trout were injected intraperitoneally with 0.01-1.0 and 1-50mg/kg of IVM or EB, respectively either alone or in combination with cyclosporin A (CsA: a P-gp substrate) at 1mg/kg. IVM affected the swimming performance (critical swimming speed, burst swimming distance, and schooling) at significantly lower concentrations than EB. When fish were exposed to IVM or EB in the presence of CsA, alterations to swimming were increased, suggesting that competition for P-gp in the BBB by CsA increased IVM and EB penetration into the CNS and decreased swimming capabilities. The effect of co-administration of CsA on swimming-related toxicity was different between IVM and EB-treated fish; EB toxicity was increased to a greater extent than IVM toxicity.
2.Anthelmintic efficacy of 22,23-dihydroavermectin B1 against gastrointestinal nematodes in calves.
Benz GW, Ernst JV. Am J Vet Res. 1981 Aug;42(8):1409-11.
Anthelmintic activities of 22,23-dihydroavermectin B1 (comprised to greater than or equal to 95% 22,23-dihydroavermectin B1a and less than or equal to 5% 22,23-dihydroavermectin B1b) against gastrointestinal nematodes in calves were evaluated in 2 controlled experiments. Infective larvae of Haemonchus contortus, Ostertagia ostertagi, Trichostrongylus axei, T colubriformis, Cooperia oncophora, and C punctate were given to 11-week-old calves and Oesophagostomum radiatum had been given 21 days earlier to allow all larvae to attain adulthood at the same time. Each experiment had 4 groups of 5 calves each. Treatment was given to the calves at 14 weeks of age, and 7 to 8 days after treatment, the calves were necropsied. In experiment 1, group 1 control calves had a geometric mean of 11,054 nematodes; groups 2, 3, and 4 calves (at 14 weeks of age) given 22,23-dihydroavermectin B1 orally at doses of 50, 100, or 200 microgram/kg had reductions of 73.
3.Anthelmintic efficacy of ivermectin against immature gastrointestinal pulmonary nematodes of calves.
Benz GW, Ernst JV. Am J Vet Res. 1981 Dec;42(12):2097-8.
Anthelmintic efficacy of ivermectin (greater than or equal to 80% 22,23-dihydroavermectin B1a and less than or equal to 20% 22,23-dihydroavermectin B1b) was evaluated in a controlled experiment against immature nematodes. Twenty calves raised to about 8 weeks of age under nematode-free conditions were allocated into 4 groups. Infective larvae of Haemonchus contortus, Ostertagia ostertagi, Trichostrongylus axei, T colubriformis, Cooperia oncophora, C punctata, Oesophagostomum radiatum, and Dictyocaulus viviparus were given orally to each calf on a staggered schedule 6 to 14 days before treatments. The drug was given subcutaneously when the nematodes were in the early 4th stage of development, and the calves were killed 23 or 24 days later. Group 1 nonmedicated control calves had a geometric mean of 25,102 nematodes; groups 2, 3, and 4 calves given ivermectin at dose rates of 50, 100, or 200 micrograms/kg had reductions of 88.2%, 98.0%, and 99.
4.Construction of ivermectin producer by domain swaps of avermectin polyketide synthase in Streptomyces avermitilis.
Zhang X1, Chen Z, Li M, Wen Y, Song Y, Li J. Appl Microbiol Biotechnol. 2006 Oct;72(5):986-94. Epub 2006 May 16.
Ivermectin, 22, 23-dihydroavermectin B1, is commercially important in human, veterinary medicine, and pesticides. It is currently synthesized by chemical reduction of the double bond between C22 and C23 of avermectins B1, which are a mixture of B1a (>80%) and B1b (<20%) produced by fermentation of Streptomyces avermitilis. The cost of ivermectin is much higher than that of avermectins B1 owing to the necessity of region-specific hydrogenation at C22-C23 of avermectins B1 with rhodium chloride as the catalyst for producing ivermectin. Here we report that ivermectin can be produced directly by fermentation of recombinant strains constructed through targeted genetic engineering of the avermectin polyketide synthase (PKS) in S. avermitilis Olm73-12, which produces only avermectins B and not avermectins A and oligomycin. The DNA region encoding the dehydratase (DH) and ketoreductase (KR) domains of module 2 from the avermectin PKS in S.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C47H72O14
Molecular Weight (Monoisotopic Mass): 860.4922 Da
Molecular Weight (Avergae Mass): 861.0662 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C47H72O14
Molecular Weight (Monoisotopic Mass): 860.4922 Da
Molecular Weight (Avergae Mass): 861.0662 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
