A Novel Drug-Drug Salt of Naproxen and Vortioxetine: Synthesis, Characterization, and Solubility Study

<table class="table-group" id="tab2"><tr><td><table class="table"><tr><td class="thead-hr" colspan="5"><hr/></td></tr><tr class="thead"><td class="align_left">H-bond</td><td class="align_center">d (D−H)</td><td class="align_center">d (H⋯A)</td><td class="align_center">d (D⋯A)</td><td class="align_center">∠ (DHA)</td></tr><tr><td class="thead-hr" colspan="5"><hr/></td></tr><tr><td class="align_left">N1-H1C<sup>+</sup>⋯O2<sup>i</sup></td><td class="align_center">0.91</td><td class="align_center">1.88</td><td class="align_center">2.742 (5)</td><td class="align_center">154</td></tr><tr><td class="align_left">N1-H1D<sup>+</sup>⋯O1<sup>ii</sup></td><td class="align_center">1.03</td><td class="align_center">1.68</td><td class="align_center">2.700 (3)</td><td class="align_center">171</td></tr><tr class="table-tr"><td colspan="5"><hr class="tbody-hr"/></td></tr></table></td></tr><tr class="table-fn"><td><div>Symmetry codes: (i) <i>x</i>, <span class="nowrap"><svg height="12.7178pt" id="M3" 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635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 35 62 22C75 10 116 -12 162 -12C234 -12 424 62 424 224C424 297 373 359 285 376V378Z"></path></g><g transform="matrix(.013,0,0,-0.013,34.842,0)"><path d="M368 703H309L44 -163H104L368 703Z"></path></g><g transform="matrix(.013,0,0,-0.013,40.204,0)"><path d="M412 140C382 77 369 73 315 73H129L270 222C362 320 402 379 402 466C402 571 322 635 234 635C177 635 130 609 99 576L42 495L64 475C90 514 133 568 201 568C274 568 318 519 318 435C318 349 255 267 193 193C144 135 87 78 32 23V0H405C417 45 427 89 440 131L412 140Z"></path></g></svg>,</span> <span class="nowrap"><svg height="11.439pt" id="M4" style="vertical-align:-2.15067pt" version="1.1" viewbox="-0.0498162 -9.28833 37.9713 11.439" width="37.9713pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M475 445L452 468C423 436 401 426 385 426S352 427 305 436C268 443 216 448 185 448C156 448 128 425 102 382C89 360 77 338 64 304L89 291C117 340 143 380 190 380C214 380 268 376 295 373C320 370 344 371 362 374L70 101C32 65 23 36 23 18C23 5 27 -3 31 -8C36 -8 39 -6 42 -1C52 15 67 31 80 40S110 49 143 33C195 8 257 -20 290 -20C339 -20 382 11 439 129L416 148C366 74 334 55 305 55C278 55 236 68 203 81C169 94 141 100 122 96C205 170 348 308 411 376L475 445Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.381,0)"><path d="M535 230V280H323V490H265V280H52V230H265V-3H323V230H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,19.917,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g><g transform="matrix(.013,0,0,-0.013,26.157,0)"><path d="M368 703H309L44 -163H104L368 703Z"></path></g><g transform="matrix(.013,0,0,-0.013,31.518,0)"><path d="M412 140C382 77 369 73 315 73H129L270 222C362 320 402 379 402 466C402 571 322 635 234 635C177 635 130 609 99 576L42 495L64 475C90 514 133 568 201 568C274 568 318 519 318 435C318 349 255 267 193 193C144 135 87 78 32 23V0H405C417 45 427 89 440 131L412 140Z"></path></g></svg>;</span> (ii) <span class="nowrap"><svg height="12.7178pt" id="M5" style="vertical-align:-3.42947pt" version="1.1" viewbox="-0.0498162 -9.28833 58.0273 12.7178" width="58.0273pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M535 230V280H52V230H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,7.631,0)"><path d="M474 0V26C414 34 401 43 364 100L267 248C300 297 324 332 345 358C381 400 394 405 455 411V437H272V411C316 406 323 401 305 370C287 337 267 306 247 276L188 369C169 397 173 405 215 411V437H16V411C71 404 83 396 114 348L201 212C171 167 144 127 116 92C77 42 66 34 4 26V0H190V26C139 34 136 43 156 77C175 113 198 150 220 183L294 66C311 39 302 31 260 26V0H474Z"></path></g><g transform="matrix(.013,0,0,-0.013,13.793,0)"><path d="M95 130C70 130 46 113 46 88C46 72 54 64 59 64C93 55 121 33 121 -3C121 -41 93 -68 44 -88L55 -117C117 -98 186 -56 186 22C186 91 131 130 95 130Z"></path></g><g transform="matrix(.013,0,0,-0.013,18.936,0)"><path d="M556 393C556 426 537 448 514 448C496 448 478 435 471 420C468 414 462 401 466 394C473 382 480 368 480 346C480 268 392 143 338 67H336C329 163 319 253 309 330S286 448 254 448C215 448 160 383 127 337L143 311C167 344 200 373 208 373S222 365 229 320C246 214 264 66 268 -20C219 -83 131 -171 17 -239L25 -261L137 -235C248 -110 273 -79 335 8C384 77 481 215 520 287C544 332 556 363 556 393Z"></path></g><g transform="matrix(.013,0,0,-0.013,29.371,0)"><path d="M535 230V280H323V490H265V280H52V230H265V-3H323V230H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,39.907,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 35 62 22C75 10 116 -12 162 -12C234 -12 424 62 424 224C424 297 373 359 285 376V378Z"></path></g><g transform="matrix(.013,0,0,-0.013,46.148,0)"><path d="M368 703H309L44 -163H104L368 703Z"></path></g><g transform="matrix(.013,0,0,-0.013,51.509,0)"><path d="M412 140C382 77 369 73 315 73H129L270 222C362 320 402 379 402 466C402 571 322 635 234 635C177 635 130 609 99 576L42 495L64 475C90 514 133 568 201 568C274 568 318 519 318 435C318 349 255 267 193 193C144 135 87 78 32 23V0H405C417 45 427 89 440 131L412 140Z"></path></g></svg>,</span> <span class="nowrap"><svg height="11.439pt" id="M6" style="vertical-align:-2.15067pt" version="1.1" viewbox="-0.0498162 -9.28833 44.6132 11.439" width="44.6132pt" 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73H129L270 222C362 320 402 379 402 466C402 571 322 635 234 635C177 635 130 609 99 576L42 495L64 475C90 514 133 568 201 568C274 568 318 519 318 435C318 349 255 267 193 193C144 135 87 78 32 23V0H405C417 45 427 89 440 131L412 140Z"></path></g></svg>.</span><br/></div></td></tr></table>

<div>Hydrogen bond distances (Å) and angles (°) of NAP-VOT.</div>

Journal of Chemistry

tab2

Table 2

Table 2: A Novel Drug-Drug Salt of Naproxen and Vortioxetine: Synthesis, Characterization, and Solubility Study 