ABT-702 HCl
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Hodoodo CAT#: H524108

CAS#: 1188890-28-9 (HCl)

Description: ABT 702 Dihydrochloride is a potent non-nucleoside adenosine kinase inhibitor, selective over other sites of adenosine interaction like A1, A2A and A3 receptors, adenosine transporter and adenosine deaminase. It displays oral activity in animal models of pain and inflammation.


Chemical Structure

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ABT-702 HCl
CAS# 1188890-28-9 (HCl)

Theoretical Analysis

Hodoodo Cat#: H524108
Name: ABT-702 HCl
CAS#: 1188890-28-9 (HCl)
Chemical Formula: C22H21BrCl2N6O
Exact Mass: 0.00
Molecular Weight: 536.250
Elemental Analysis: C, 49.27; H, 3.95; Br, 14.90; Cl, 13.22; N, 15.67; O, 2.98

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 1950 2 Weeks
1g USD 2950 2 Weeks
2g USD 5450 2 Weeks
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Related CAS #: 214697-26-4 (free base)   1188890-28-9 (HCl)    

Synonym: ABT 702 Dihydrochloride; ABT 702; ABT-702; ABT702; ABT-702 HCl; ABT-702 hydrochloride

IUPAC/Chemical Name: 5-(3-bromophenyl)-7-(6-morpholinopyridin-3-yl)pyrido[2,3-d]pyrimidin-4-amine dihydrochloride

InChi Key: OOXNYFKPOPJIOT-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H19BrN6O.2ClH/c23-16-3-1-2-14(10-16)17-11-18(28-22-20(17)21(24)26-13-27-22)15-4-5-19(25-12-15)29-6-8-30-9-7-29;;/h1-5,10-13H,6-9H2,(H2,24,26,27,28);2*1H

SMILES Code: BrC1=CC(C2=CC(C3=CC=C(N4CCOCC4)N=C3)=NC5=NC=NC(N)=C52)=CC=C1.[H]Cl.[H]Cl

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:

Biological target: ABT-702 dihydrochloride is a potent adenosine kinase (AK) inhibitor (IC50=1.7 nM).
In vitro activity: To identify the AR subtype(s) involved in ABT 702 inhibitory effect on TNF-α release in the retinal microglia in response to AGA, this study examined the effect of the ABT 702 in the presence of AR subtype-selective antagonists. As shown in Fig. 9, cells pretreated with vehicle showed a significant increase in AGA-induced TNF-α release compared with vehicle-treated control cells. Treatment with ABT 702 at a concentration of 20 μM potently inhibited AGA-induced TNF-α release. Reference: Life Sci. 2013 Jul 30;93(2-3):78-88. https://pubmed.ncbi.nlm.nih.gov/23770229/
In vivo activity: Bath application of ABT-702 (3 μM) to the isolated neonatal rat spinal cord for 20 min gradually decreased sVRPs with a slight decline in MSRs, which were both rapidly recovered by 8CPT (3 μM), an adenosine A1 receptor antagonist (Fig. 1A). On the other hand, both sVRP and MSR inhibitions by ABT-702 were not affected by potent and selective adenosine A2A, A2B and A3 receptor antagonists, ZM241385 (0.1 μM), PSB1115 (0.1 μM) and VUF5574 (0.1 μM), respectively (Fig. 1C and D). Reference: Neuropharmacology. 2015 Oct;97:160-70. https://pubmed.ncbi.nlm.nih.gov/26066576/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 66.7 124.33
Ethanol 3.0 5.59

Preparing Stock Solutions

The following data is based on the product molecular weight 536.25 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. Elsherbiny NM, Ahmad S, Naime M, Elsherbini AM, Fulzele S, Al-Gayyar MM, Eissa LA, El-Shishtawy MM, Liou GI. ABT-702, an adenosine kinase inhibitor, attenuates inflammation in diabetic retinopathy. Life Sci. 2013 Jul 30;93(2-3):78-88. doi: 10.1016/j.lfs.2013.05.024. Epub 2013 Jun 12. PMID: 23770229. 2. Otsuguro K, Tomonari Y, Otsuka S, Yamaguchi S, Kon Y, Ito S. An adenosine kinase inhibitor, ABT-702, inhibits spinal nociceptive transmission by adenosine release via equilibrative nucleoside transporters in rat. Neuropharmacology. 2015 Oct;97:160-70. doi: 10.1016/j.neuropharm.2015.05.035. Epub 2015 Jun 9. PMID: 26066576. 3. Elsherbiny NM, Ahmad S, Naime M, Elsherbini AM, Fulzele S, Al-Gayyar MM, Eissa LA, El-Shishtawy MM, Liou GI. ABT-702, an adenosine kinase inhibitor, attenuates inflammation in diabetic retinopathy. Life Sci. 2013 Jul 30;93(2-3):78-88. doi: 10.1016/j.lfs.2013.05.024. Epub 2013 Jun 12. PMID: 23770229.
In vitro protocol: 1. Elsherbiny NM, Ahmad S, Naime M, Elsherbini AM, Fulzele S, Al-Gayyar MM, Eissa LA, El-Shishtawy MM, Liou GI. ABT-702, an adenosine kinase inhibitor, attenuates inflammation in diabetic retinopathy. Life Sci. 2013 Jul 30;93(2-3):78-88. doi: 10.1016/j.lfs.2013.05.024. Epub 2013 Jun 12. PMID: 23770229.
In vivo protocol: 1. Otsuguro K, Tomonari Y, Otsuka S, Yamaguchi S, Kon Y, Ito S. An adenosine kinase inhibitor, ABT-702, inhibits spinal nociceptive transmission by adenosine release via equilibrative nucleoside transporters in rat. Neuropharmacology. 2015 Oct;97:160-70. doi: 10.1016/j.neuropharm.2015.05.035. Epub 2015 Jun 9. PMID: 26066576. 2. Elsherbiny NM, Ahmad S, Naime M, Elsherbini AM, Fulzele S, Al-Gayyar MM, Eissa LA, El-Shishtawy MM, Liou GI. ABT-702, an adenosine kinase inhibitor, attenuates inflammation in diabetic retinopathy. Life Sci. 2013 Jul 30;93(2-3):78-88. doi: 10.1016/j.lfs.2013.05.024. Epub 2013 Jun 12. PMID: 23770229.

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1: An G, Liu W, Duan WR, Nothaft W, Awni W, Dutta S. Population pharmacokinetics and exposure-uric acid analyses after single and multiple doses of ABT-639, a calcium channel blocker, in healthy volunteers. AAPS J. 2015 Mar;17(2):416-26. doi: 10.1208/s12248-014-9709-1. Epub 2015 Jan 8. Erratum in: AAPS J. 2015 Mar;17(2):481-92. PMID: 25567367; PMCID: PMC4365099.


2: Jarvis MF, Scott VE, McGaraughty S, Chu KL, Xu J, Niforatos W, Milicic I, Joshi S, Zhang Q, Xia Z. A peripherally acting, selective T-type calcium channel blocker, ABT-639, effectively reduces nociceptive and neuropathic pain in rats. Biochem Pharmacol. 2014 Jun 15;89(4):536-44. doi: 10.1016/j.bcp.2014.03.015. Epub 2014 Apr 12. PMID: 24726441.


3: Zhang Q, Xia Z, Joshi S, Scott VE, Jarvis MF. Optimization of ADME Properties for Sulfonamides Leading to the Discovery of a T-Type Calcium Channel Blocker, ABT-639. ACS Med Chem Lett. 2015 Apr 28;6(6):641-4. doi: 10.1021/acsmedchemlett.5b00023. PMID: 26101566; PMCID: PMC4468402.


4: Ziegler D, Duan WR, An G, Thomas JW, Nothaft W. A randomized double-blind, placebo-, and active-controlled study of T-type calcium channel blocker ABT-639 in patients with diabetic peripheral neuropathic pain. Pain. 2015 Oct;156(10):2013-2020. doi: 10.1097/j.pain.0000000000000263. PMID: 26067585; PMCID: PMC4770341.


5: Wallace M, Duan R, Liu W, Locke C, Nothaft W. A Randomized, Double-Blind, Placebo-Controlled, Crossover Study of the T-Type Calcium Channel Blocker ABT-639 in an Intradermal Capsaicin Experimental Pain Model in Healthy Adults. Pain Med. 2016 Mar;17(3):551-560. doi: 10.1093/pm/pnv068. Epub 2015 Dec 16. PMID: 26814294.


6: An G, Liu W, Duan WR, Nothaft W, Awni W, Dutta S. Erratum to: population pharmacokinetics and exposure-uric acid analyses after single and multiple doses of ABT-639, a calcium channel blocker, in healthy volunteers. AAPS J. 2015 Mar;17(2):481-92. doi: 10.1208/s12248-015-9725-9. Erratum for: AAPS J. 2015 Mar;17(2):416-26. PMID: 25676842; PMCID: PMC4365100.


7: Serra J, Duan WR, Locke C, Solà R, Liu W, Nothaft W. Effects of a T-type calcium channel blocker, ABT-639, on spontaneous activity in C-nociceptors in patients with painful diabetic neuropathy: a randomized controlled trial. Pain. 2015 Nov;156(11):2175-2183. doi: 10.1097/j.pain.0000000000000249. PMID: 26035253.


8: Tibbs GR, Posson DJ, Goldstein PA. Voltage-Gated Ion Channels in the PNS: Novel Therapies for Neuropathic Pain? Trends Pharmacol Sci. 2016 Jul;37(7):522-542. doi: 10.1016/j.tips.2016.05.002. Epub 2016 May 24. PMID: 27233519.


9: Wang MX, Liu X, Li JM, Liu L, Lu W, Chen GC. Inhibition of CACNA1H can alleviate endoplasmic reticulum stress and reduce myocardial cell apoptosis caused by myocardial infarction. Eur Rev Med Pharmacol Sci. 2020 Dec;24(24):12887-12895. doi: 10.26355/eurrev_202012_24192. PMID: 33378039.


10: Liu S, Ba Y, Li C, Xu G. Inactivation of CACNA1H induces cell apoptosis by initiating endoplasmic reticulum stress in glioma. Transl Neurosci. 2023 May 26;14(1):20220285. doi: 10.1515/tnsci-2022-0285. PMID: 37250140; PMCID: PMC10224624.


11: Hu J, Wu Q, Wang Z, Hong J, Chen R, Li B, Hu Z, Hu X, Zhang M. Inhibition of CACNA1H attenuates doxorubicin-induced acute cardiotoxicity by affecting endoplasmic reticulum stress. Biomed Pharmacother. 2019 Dec;120:109475. doi: 10.1016/j.biopha.2019.109475. Epub 2019 Sep 30. PMID: 31580970.


12: Picard E, Carvalho FA, Agosti F, Bourinet E, Ardid D, Eschalier A, Daulhac L, Mallet C. Inhibition of Cav 3.2 calcium channels: A new target for colonic hypersensitivity associated with low-grade inflammation. Br J Pharmacol. 2019 Apr;176(7):950-963. doi: 10.1111/bph.14608. Epub 2019 Mar 11. PMID: 30714145; PMCID: PMC6433640.


13: Wu H, Xie X, Sun M, Chen M, Tao X, Fang X, Meng X, Wei W, Yu M. Modification of mesenchymal stem cells by HMGB1 promotes the activity of Cav3.2 T-type calcium channel via PKA/β-catenin/γ-cystathionase pathway. Stem Cell Res Ther. 2022 Jan 10;13(1):4. doi: 10.1186/s13287-021-02677-z. PMID: 35012644; PMCID: PMC8744322.


14: Grundy L, Tay C, Christie S, Harrington AM, Castro J, Cardoso FC, Lewis RJ, Zagorodnyuk V, Brierley SM. The T-type calcium channel Ca V 3.2 regulates bladder afferent responses to mechanical stimuli. Pain. 2023 May 1;164(5):1012-1026. doi: 10.1097/j.pain.0000000000002795. Epub 2022 Oct 21. PMID: 36279179; PMCID: PMC10108591.


15: Teleb M, Zhang FX, Huang J, Gadotti VM, Farghaly AM, AboulWafa OM, Zamponi GW, Fahmy H. Synthesis and biological evaluation of novel N3-substituted dihydropyrimidine derivatives as T-type calcium channel blockers and their efficacy as analgesics in mouse models of inflammatory pain. Bioorg Med Chem. 2017 Mar 15;25(6):1926-1938. doi: 10.1016/j.bmc.2017.02.015. Epub 2017 Feb 13. PMID: 28233679.


16: Picard E, Kerckhove N, François A, Boudieu L, Billard E, Carvalho FA, Bogard G, Gosset P, Bourdier J, Aissouni Y, Bourinet E, Eschalier A, Daulhac L, Mallet C. Role of T CD4+ cells, macrophages, C-low threshold mechanoreceptors and spinal Cav 3.2 channels in inflammation and related pain-like symptoms in murine inflammatory models. Br J Pharmacol. 2023 Feb;180(4):385-400. doi: 10.1111/bph.15956. Epub 2022 Nov 14. PMID: 36131381.