Doxapram
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MedKoo CAT#: 319509

CAS#: 309-29-5 (free)

Description: Doxapram is a respiratory stimulant. Administered intravenously, Doxapram stimulates an increase in tidal volume and respiratory rate. Doxapram stimulates chemoreceptors in the carotid bodies of the carotid arteries, which in turn, stimulates the respiratory centre in the brain stem. Doxapram induced changes in the electrophysiological properties of pre-inspiratory and inspiratory neurones. Results suggest that respiratory activity enhancement was likely to be induced via effects on the potassium channels of pre-inspiratory and inspiratory neurones and indicate the central actions of doxapram.


Chemical Structure

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Doxapram
CAS# 309-29-5 (free)

Theoretical Analysis

MedKoo Cat#: 319509
Name: Doxapram
CAS#: 309-29-5 (free)
Chemical Formula: C24H30N2O2
Exact Mass: 378.23
Molecular Weight: 378.516
Elemental Analysis: C, 76.16; H, 7.99; N, 7.40; O, 8.45

Price and Availability

Size Price Availability Quantity
100mg USD 850 2 weeks
200mg USD 1250 2 weeks
500mg USD 1650 2 weeks
1g USD 2950 2 weeks
2g USD 4250 2 weeks
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Related CAS #: 309-29-5 (free)   7081-53-0 (HCl)    

Synonym: AHR-619; AHR 619; AHR619; Doxapram; Doxapram hydrochloride, Brand name Dopram, Stimulex or Respiram.

IUPAC/Chemical Name: 1-ethyl-4- (2-morpholin-4-ylethyl)- 3,3-diphenyl-pyrrolidin-2-one

InChi Key: XFDJYSQDBULQSI-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H30N2O2/c1-2-26-19-22(13-14-25-15-17-28-18-16-25)24(23(26)27,20-9-5-3-6-10-20)21-11-7-4-8-12-21/h3-12,22H,2,13-19H2,1H3

SMILES Code: O=C1N(CC)CC(CCN2CCOCC2)C1(C3=CC=CC=C3)C4=CC=CC=C4

Appearance: White to off-white crystalline 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:
Biological target: Doxapram inhibits TASK-1, TASK-3, TASK-1/TASK-3 heterodimeric channel function with EC50 of 410 nM, 37 μM, 9 μM, respectively.
In vitro activity: Doxapram inhibited TASK-1 (half-maximal effective concentration [EC50], 410 nM), TASK-3 (EC50, 37 microM), and TASK-1/TASK-3 heterodimeric channel function (EC50, 9 microM). Chimera studies suggested that the carboxy terminus of TASK-1 is important for doxapram inhibition. Reference: Anesth Analg. 2006 Mar;102(3):779-85. https://pubmed.ncbi.nlm.nih.gov/16492828/
In vivo activity: The present study investigated the effects of doxapram on membrane potential and synaptic transmission using intracellular recordings of larval Drosophila muscles. Doxapram (1 mM and 10 mM) depolarizes the muscle and appears to depolarize motor neurons, causing an increase in the frequency of spontaneous quantal events and evoked excitatory junction potentials. Reference: Comp Biochem Physiol C Toxicol Pharmacol. 2023 Jan;263:109497. https://pubmed.ncbi.nlm.nih.gov/36306997/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 75.0 198.14
Ethanol 75.0 198.14

Preparing Stock Solutions

The following data is based on the product molecular weight 378.52 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. Cotten JF, Keshavaprasad B, Laster MJ, Eger EI 2nd, Yost CS. The ventilatory stimulant doxapram inhibits TASK tandem pore (K2P) potassium channel function but does not affect minimum alveolar anesthetic concentration. Anesth Analg. 2006 Mar;102(3):779-85. doi: 10.1213/01.ane.0000194289.34345.63. PMID: 16492828. 2. Anderson-Beck R, Wilson L, Brazier S, Hughes IE, Peers C. Doxapram stimulates dopamine release from the intact rat carotid body in vitro. Neurosci Lett. 1995 Feb 24;187(1):25-8. doi: 10.1016/0304-3940(95)11328-t. PMID: 7617294. 3. Vacassenno RM, Haddad CN, Cooper RL. The effects of doxapram (blocker of K2p channels) on resting membrane potential and synaptic transmission at the Drosophila neuromuscular junction. Comp Biochem Physiol C Toxicol Pharmacol. 2023 Jan;263:109497. doi: 10.1016/j.cbpc.2022.109497. Epub 2022 Oct 25. PMID: 36306997. 4. Wiedmann F, Beyersdorf C, Zhou XB, Kraft M, Paasche A, Jávorszky N, Rinné S, Sutanto H, Büscher A, Foerster KI, Blank A, El-Battrawy I, Li X, Lang S, Tochtermann U, Kremer J, Arif R, Karck M, Decher N, van Loon G, Akin I, Borggrefe M, Kallenberger S, Heijman J, Haefeli WE, Katus HA, Schmidt C. Treatment of atrial fibrillation with doxapram: TASK-1 potassium channel inhibition as a novel pharmacological strategy. Cardiovasc Res. 2022 Jun 22;118(7):1728-1741. doi: 10.1093/cvr/cvab177. PMID: 34028533.
In vitro protocol: 1. Cotten JF, Keshavaprasad B, Laster MJ, Eger EI 2nd, Yost CS. The ventilatory stimulant doxapram inhibits TASK tandem pore (K2P) potassium channel function but does not affect minimum alveolar anesthetic concentration. Anesth Analg. 2006 Mar;102(3):779-85. doi: 10.1213/01.ane.0000194289.34345.63. PMID: 16492828. 2. Anderson-Beck R, Wilson L, Brazier S, Hughes IE, Peers C. Doxapram stimulates dopamine release from the intact rat carotid body in vitro. Neurosci Lett. 1995 Feb 24;187(1):25-8. doi: 10.1016/0304-3940(95)11328-t. PMID: 7617294.
In vivo protocol: 1. Vacassenno RM, Haddad CN, Cooper RL. The effects of doxapram (blocker of K2p channels) on resting membrane potential and synaptic transmission at the Drosophila neuromuscular junction. Comp Biochem Physiol C Toxicol Pharmacol. 2023 Jan;263:109497. doi: 10.1016/j.cbpc.2022.109497. Epub 2022 Oct 25. PMID: 36306997. 2. Wiedmann F, Beyersdorf C, Zhou XB, Kraft M, Paasche A, Jávorszky N, Rinné S, Sutanto H, Büscher A, Foerster KI, Blank A, El-Battrawy I, Li X, Lang S, Tochtermann U, Kremer J, Arif R, Karck M, Decher N, van Loon G, Akin I, Borggrefe M, Kallenberger S, Heijman J, Haefeli WE, Katus HA, Schmidt C. Treatment of atrial fibrillation with doxapram: TASK-1 potassium channel inhibition as a novel pharmacological strategy. Cardiovasc Res. 2022 Jun 22;118(7):1728-1741. doi: 10.1093/cvr/cvab177. PMID: 34028533.

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1: Martinez JM, Garakani A, Aaronson CJ, Gorman JM. Heart rate and respiratory response to doxapram in patients with panic disorder. Psychiatry Res. 2015 May 30;227(1):32-8. doi: 10.1016/j.psychres.2015.03.001. Epub 2015 Mar 9. PubMed PMID: 25819170; PubMed Central PMCID: PMC4420657.

2: Wang HL, Tang SH, Wang XQ, Gong WH, Liu XM, Lei WF. Doxapram hastens the recovery following total intravenous anesthesia with dexmedetomidine, propofol and remifentanil. Exp Ther Med. 2015 Apr;9(4):1518-1522. Epub 2015 Feb 2. PubMed PMID: 25780462; PubMed Central PMCID: PMC4353763.

3: Ogawa Y, Irikura M, Kobaru Y, Tomiyasu M, Kochiyama Y, Uriu M, Ishitsuka Y, Kondo Y, Yukawa E, Kamada N, Ohno H, Yamazaki T, Irie T. Population pharmacokinetics of doxapram in low-birth-weight Japanese infants with apnea. Eur J Pediatr. 2015 Apr;174(4):509-18. doi: 10.1007/s00431-014-2416-1. Epub 2014 Sep 25. PubMed PMID: 25248340.

4: Czaba-Hnizdo C, Olischar M, Rona Z, Weninger M, Berger A, Klebermass-Schrehof K. Amplitude-integrated electroencephalography shows that doxapram influences the brain activity of preterm infants. Acta Paediatr. 2014 Sep;103(9):922-7. doi: 10.1111/apa.12681. Epub 2014 May 27. PubMed PMID: 24813556.

5: Osaka Y, Onimaru H, Kotani S, Kashiwagi M, Morisaki H, Takeda J. The effects of doxapram on medullary respiratory neurones in brainstem-spinal cord preparations from newborn rats. Anaesthesia. 2014 May;69(5):468-75. doi: 10.1111/anae.12590. Epub 2014 Mar 7. PubMed PMID: 24601902.

6: Oikawa S, Nomura H, Nishio M, Nagata R, Hata T. Doxapram hydrochloride aggravates adrenaline-induced arrhythmias accompanied by bidirectional ventricular tachycardia. ISRN Cardiol. 2014 Jan 9;2014:212045. doi: 10.1155/2014/212045. eCollection 2014. PubMed PMID: 24527224; PubMed Central PMCID: PMC3912761.

7: Prins SA, Pans SJ, van Weissenbruch MM, Walther FJ, Simons SH. Doxapram use for apnoea of prematurity in neonatal intensive care. Int J Pediatr. 2013;2013:251047. doi: 10.1155/2013/251047. Epub 2013 Nov 26. PubMed PMID: 24376463; PubMed Central PMCID: PMC3860126.

8: Sandhu MS, Lee KZ, Gonzalez-Rothi EJ, Fuller DD. Repeated intravenous doxapram induces phrenic motor facilitation. Exp Neurol. 2013 Dec;250:108-15. doi: 10.1016/j.expneurol.2013.08.016. Epub 2013 Sep 4. PubMed PMID: 24013015; PubMed Central PMCID: PMC3844021.

9: Zapata M, Hofmeister EH. Refinement of the dose of doxapram to counteract the sedative effects of acepromazine in dogs. J Small Anim Pract. 2013 Aug;54(8):405-8. doi: 10.1111/jsap.12105. PubMed PMID: 23879828.

10: Kim DW, Joo JD, In JH, Jeon YS, Jung HS, Jeon KB, Park JS, Choi JW. Comparison of the recovery and respiratory effects of aminophylline and doxapram following total intravenous anesthesia with propofol and remifentanil. J Clin Anesth. 2013 May;25(3):173-6. doi: 10.1016/j.jclinane.2012.07.005. Epub 2013 Apr 11. PubMed PMID: 23583458.

11: Fischer C, Ferdynus C, Gouyon JB, Semama DS. Doxapram and hypokalaemia in very preterm infants. Arch Dis Child Fetal Neonatal Ed. 2013 Sep;98(5):F416-8. doi: 10.1136/archdischild-2012-303089. Epub 2013 Feb 28. PubMed PMID: 23448699.

12: Bleul U, Bylang T. Effects of doxapram, prethcamide and lobeline on spirometric, blood gas and acid-base variables in healthy new-born calves. Vet J. 2012 Nov;194(2):240-6. doi: 10.1016/j.tvjl.2012.04.007. Epub 2012 May 18. PubMed PMID: 22609153.

13: Towards evidence based emergency medicine:PRIVATE best BETs from the Manchester Royal Infirmary. Bet 2: doxapram resurrected? Weak evidence of efficacy suggests a potential use in patients ineligible for non-invasive ventilation. Emerg Med J. 2012 Jan;29(1):78-80. doi: 10.1136/emermed-2011-200981. Review. PubMed PMID: 22186269.

14: Bamgbade OA. Advantages of doxapram for post-anaesthesia recovery and outcomes in bariatric surgery patients with obstructive sleep apnoea. Eur J Anaesthesiol. 2011 May;28(5):387-8. doi: 10.1097/EJA.0b013e328342956b. PubMed PMID: 21191303.

15: Meyer LC, Hetem RS, Fick LG, Mitchell D, Fuller A. Effects of serotonin agonists and doxapram on respiratory depression and hypoxemia in etorphine-immobilized impala (Aepyceros melampus). J Wildl Dis. 2010 Apr;46(2):514-24. PubMed PMID: 20688644.

16: Shrestha AB. Comparative study on effectiveness of doxapram and pethidine for postanaesthetic shivering. JNMA J Nepal Med Assoc. 2009 Apr-Jun;48(174):116-20. PubMed PMID: 20387350.

17: Li GC, Jiao YG, Wu ZH, Fang F, Cheng J. [Effect of doxapram on the respiratory rhythmical discharge activity in the brainstem slice of neonatal rats]. Nan Fang Yi Ke Da Xue Xue Bao. 2010 Feb;30(2):245-8. Chinese. PubMed PMID: 20159691.

18: Li GC, Zhang HT, Jiao YG, Wu ZH, Fang F, Cheng J. Glial cells are involved in the exciting effects of doxapram on brainstem slices in vitro. Cell Mol Neurobiol. 2010 Jul;30(5):667-70. doi: 10.1007/s10571-010-9500-5. Epub 2010 Feb 7. PubMed PMID: 20140700.

19: Bleul U, Bircher B, Jud RS, Kutter AP. Respiratory and cardiovascular effects of doxapram and theophylline for the treatment of asphyxia in neonatal calves. Theriogenology. 2010 Mar 15;73(5):612-9. doi: 10.1016/j.theriogenology.2009.10.017. PubMed PMID: 20022095.

20: Li E, Sritharan G, Mogos M, Roffey P, Thangathurai D. Doxapram revisited in patients with cancer. J Palliat Med. 2009 Aug;12(8):673. doi: 10.1089/jpm.2009.0073. PubMed PMID: 19663568.